Design, synthesis and biological evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal agents

Article abstract of DOI:10.1016/j.ejmech.2015.11.029

A series of chalconyl blended triazole allied silatranes (7a-g/8a-g/9a-g) were synthesized in good yields using a simple, economical and biocompatible synthetic route. The blend of three different pharmacologically active moieties into a single scaffold r

Full text of DOI:10.1016/j.ejmech.2015.11.029

Accepted Manuscript
Design, Synthesis and biological evaluation of chalconyl blended triazole allied
organosilatranes as giardicidal and trichomonacidal agents
Dr. Gurjaspreet Singh, Assistant Professor, Aanchal Arora, Satinderpal Singh
Mangat, Sunita Rani, Hargobinder Kaur, Kapil Goyal, Rakesh Sehgal, Indresh Kumar
Maurya, Rupinder Tewari, Duane Choquesillo-Lazarte, Subash Sahoo, Navneet Kaur
PII:
S0223-5234(15)30366-4
10.1016/j.ejmech.2015.11.029
EJMECH 8219
DOI:
Reference:
To appear in: European Journal of Medicinal Chemistry
Received Date: 27 August 2015
Revised Date: 14 November 2015
Accepted Date: 18 November 2015
Please cite this article as: G. Singh, A. Arora, S.S. Mangat, S. Rani, H. Kaur, K. Goyal, R. Sehgal,
I.K. Maurya, R. Tewari, D. Choquesillo-Lazarte, S. Sahoo, N. Kaur, Design, Synthesis and biological
evaluation of chalconyl blended triazole allied organosilatranes as giardicidal and trichomonacidal
agents, European Journal of Medicinal Chemistry (2015), doi: 10.1016/j.ejmech.2015.11.029.
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ACCEPTED MANUSCRIPT
Design, Synthesis and biological evaluation of chalconyl blended triazole allied
organosilatranes as giardicidal and trichomonacidal agents
a, *
a
a
a
Gurjaspreet Singh , Aanchal Arora , Satinderpal Singh Mangat , Sunita Rani , Hargobinder
b
b
b
c
c
Kaur , Kapil Goyal , Rakesh Sehgal , Indresh Kumar Maurya , Rupinder Tewari , Duane
d
a
e
Choquesillo-Lazarte , Subash Sahoo , Navneet Kaur
a
Department of Chemistry and Centre of Advanced Studies, Panjab University, Chandigarh,
1
60014, India
b
Department of Medical Parasitology, Post graduate Institute of Medical Education and
Research, Chandigarh, 160024, India
c
Department of Microbial Biotechnology, Panjab University, Chandigarh, 160014, India
d
Laboratorio de Estudios Cristalográficos, IACT-CSIC. Avda. de las Palmeras 4, 18100 -
Armilla (Granada), Spain
e
Centre for Nano-science and Nano-technology, Panjab University, Chandigarh, 160014,
India
*
Corresponding Author
Dr. Gurjaspreet Singh
Assistant Professor
Department of Chemistry and Centre of Advanced Studies
Panjab University, Chandigarh
India
+91-0172-2534428
Email: gjpsingh@pu.ac.in

ACCEPTED MANUSCRIPT
A series of 1,2,3-triazole and chalcone allied organosilatranes (7a-7g,8a-8g,9a-9g) are
synthesized and well characterized by various spectroscopic techniques. The synthesized
compounds are passed through the computer based screeing for their physicochemical
properties and then tested for their antigiardial and antitrichomonal activities. The compounds
showing good activites are then tested for their cytotoxicity against Hek-293 and HeLa cells.

ACCEPTED MANUSCRIPT

ACCEPTED MANUSCRIPT
Design, Synthesis and biological evaluation of chalconyl blended triazole allied
organosilatranes as giardicidal and trichomonacidal agents
a, *
a
a
a
Gurjaspreet Singh , Aanchal Arora , Satinderpal Singh Mangat , Sunita Rani , Hargobinder
b
b
b
c
c
Kaur , Kapil Goyal , Rakesh Sehgal , Indresh Kumar Maurya , Rupinder Tewari , Duane
d
a
e
Choquesillo-Lazarte , Subash Sahoo , Navneet Kaur
a
Department of Chemistry and Centre of Advanced Studies, Panjab University, Chandigarh,
1
60014, India
b
Department of Medical Parasitology, Post graduate Institute of Medical Education and
Research, Chandigarh, 160024, India
c
Department of Microbial Biotechnology, Panjab University, Chandigarh, 160014, India
d
Laboratorio de Estudios Cristalográficos, IACT-CSIC. Avda. de las Palmeras 4, 18100 -
Armilla (Granada), Spain
e
Centre for Nano-science and Nano-technology, Panjab University, Chandigarh, 160014,
India
*
Corresponding Author
Dr. Gurjaspreet Singh
Assistant Professor
Department of Chemistry and Centre of Advanced Studies
Panjab University, Chandigarh
India
+91-0172-2534428
Email: gjpsingh@pu.ac.in
1

ACCEPTED MANUSCRIPT
Abstract
A series of chalconyl blended triazole allied silatranes (7a-7g/8a-8g/9a-9g) were synthesized
in good yields using a simple, economical and biocompatible synthetic route. The blend of
three different pharmacologically active moieties into a single scaffold resulted into
synergistic effect in their bio-activity. Various substitutions were tried to study the structure
activity relationship (SAR) of the synthesized compounds on the basis of biological results.
1
13
All the newly synthesized compounds were well characterized by IR, H and C NMR, low
resolution mass spectroscopy and elemental analysis. The structures of 7a and 7c were
authenticated by single crystal X-ray crystallography. These compounds were screened by
using Molinspiration software for their physicochemical properties and all the compounds
showed good oral bioavailability. The antiparasitic activity of the newly synthesized
compounds was evaluated against unicellular parasites (Giardia lamblia and Trichomonas
vaginalis) in comparison to standard drug (metronidazole) by 3-(4,5-Dimethylthiazol-yl)-
diphenyl tetrazoliumbromide (MTT) assay. All the compounds displayed significant activity
against G. lamblia and T. vaginalis with IC values ranging from 19.58-131.2 µM and 18.24-
5
0
1
01.26 µM respectively. The entire library of compounds was found to be more active than
metronidazole except 9a, 9f and 9g. Notably, 9e and 7e were found to be most significant
against G. lamblia and T. vaginalis respectively.
Key Words: Chalcone - 1,2,3-Triazole - Silatrane - Giardicidal activity - Trichomonacidal
activity - Metronidazole - 3-(4,5-Dimethylthiazol-yl)-diphenyl tetrazoliumbromide (MTT)
1
. Introduction
Parasitic diseases are an important public health problem in developing countries [1].
Among the diarrhoea causing agents, giardiasis is an important parasitic cause, commonly
2

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treated with metronidazole [2]. Apart from causing diarrhoea, it can lead to wide range of
clinical manifestations such as abdominal pain, nausea, dehydration, vomiting, and
malabsorption syndrome producing adverse effect on growth and development [3-6]. Around
2
80 million people, especially children, are infected around the world [7-9].
Trichomoniasis is another parasitic disease caused by a single-celled protozoan parasite T.
vaginalis. It is a sexually transmitted disease leading to clinical manifestations such as
malodorous vaginal discharge, dysuria, lower abdominal pain and damage of vaginal
epithelium, increasing the risk to HIV infection and cervical neoplasia [10-13]. Most
commonly used drugs for the treatment of giardiasis and trichomoniasis are metronidazole 1
(Fig.1), tinidazole, furazolidone, paramomycin or nitazoxanide 2 (Fig. 1) [14,15].
Metronidazole affects electron transport and it is metabolized to produce a reactive
reduced form which is cytotoxic for parasites [16]. A recently reported broad spectrum
antiparasitic agent, nitroheterocycle nitazoxanide (NTZ) has got few unpleasant effects such
as nausea and vomiting [17]. Mendez et al. have latterly reported a new analog of NTZ 3
(Fig. 1) and tested their antigiardial activities [18]. These chemotherapeutic antiparasitic
agents are usually associated with several side effects such as treatment failures, activity
against normal intestinal flora, parasite resistance and possible carcinogenicity [5,19-22].
These issues lead to an imperative quest for more effective, selective and less toxic drugs to
treat both these diseases.
In the development of new drugs, it is convenient to have a range of diverse chemical
structures with the desired pharmacological activity [12]. “Molecular hybridization” is one of
the many strategies, which has been successfully applied for the design, and development of
new and efficient hybrids [23-25]. It involves the combination of two or more chemical
entities to form new hybrid moieties exhibiting additive pharmacological activities [26].
Considering this, the design of our synthesis is based on the individual activities of the
3

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selected moieties with the anticipation of their higher activity in the hybrid molecules.
Chalcones, 1,2,3-triazoles and silatranes have been investigated as important fragments
possessing wide range of biological activities.
Chalcones (1,3-diarylprop-2-en-1-one) are well known for their diverse activites such as
antileishmanial [27], antibacterial [28], antifungal [29], antitumour [30], antimalarial [31,32],
antiviral [33], antitubercular [34], antiinvasive [35], anticancer [36], antioxidant [37],
antihyperglycemic [38], antiinflammatory [39], analgesic [40], antiplatelet [41], antiulcerative
[
42] and a large list yet to be mentioned. Moreover, they can be readily synthesized by simple
and inexpensive Claisen-Schmidt reaction [43] and various modifications can be made by
introducing different substituents on the aromatic rings of chalcones to give a large number of
analogues showing immense activities [44-46].
1
,2,3-triazoles are an important class of heterocyclic compounds that received significant
attention for the past few decades because of the broad spectrum of their applications in
biochemical, pharmaceutical, and material sciences [47-60]. These are attractive connecting
units, since they are stable to metabolic degradation, oxidative/reductive conditions and
actively participate in dipole-dipole interactions and hydrogen bonding [61]. So, these
moieties can be shaped into powerful pharmacophores that can play an important role in bio-
conjugation. The copper (I) catalysed synthesis of 1,2,3-triazoles [62] from azides and
terminal alkynes is an increasingly common method for rapid synthesis of organic and
bioorganic compounds in high yields and purity [63]. Therefore, the well recognized click
route [64] is followed to generate 1,2,3-triazole derivatives.
Silatranes are intracomplex silicon triethanolamine esters of general formula XSi
(
OCH CH ) N. The unique structure, specific physicochemical properties, biological activity
2 2 3
and prospects of applications as drugs [65-70] have necessitated the search for novel effective
methods for synthesizing the new compounds of this type. The unusual trigonal bipyramidal
4

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structure of silatranes leads to their high dipole moment and high electronegativity which
favours the chemisorption of these molecules on the surface of proteins and lipid layer of
cellular membranes either by forming hydrogen bonds with equatorial oxygens or by dipole-
dipole interactions. Silatranes also form sorptive layer over cellular membranes to avoid
penetration of peroxy radicals and toxins. Their ability to donate silicon that acts as an
essential microelement for all living organisms and form triethanolamine as the hydrolysis
product which is also biologically active makes them even more fascinating [71].
In light of above findings, we are presenting an efficient way for the molecular stitching
of different pharmacophoric elements of silatranes, triazole and chalcones in a single
chemical framework resulting into a library of chalcones and further investigation of in vitro
antiparasitic activity of these compounds on intestinal unicellular parasite (G. lamblia) and a
urogenital tract parasite (T. vaginalis).
2
. Results and discussion
2
.1. Drug Design
We have designed the compounds 7a-7g/8a-8g/9a-9g on the basis of individual activities
of three different biologically potent moieties. In order to coalesce the activity of these
groups, molecular nailing was done in an efficient and productive way so that the active
group of the three moieties appear together in the final product showing some kind of
synergistic effect. Our approach is to substitute ring A of the chalcone moiety with the
triazole substituted silatrane. The drug design was also based on the computer aided
prediction of the physicochemical properties of the molecules like polar surface area, number
of rotational bonds, hydrogen bond donating or accepting ability and lipophilicity values that
play an important role in predicting the drug bioavailability [72,73]. The aim of
computational analysis is to filter the compounds considered unsuitable for screening
purposes. Polar surface area illustrates drug absorption thus predicting that the molecules
5

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with PSA > 140 have low oral bioavailability. The number of rotational bonds in a molecule
is the measure of molecule’s flexibility and is found to be a very good descriptor of drug’s
permeability. The hydrogen bonding capacity is based on the presence of oxygen and
nitrogen atoms in the molecule and somehow affects drug’s permeation rate. The lipophilic
character can be predicted from clogP values and the values ≤ 5 are considered ideal for
orally active drugs. These parameters were calculated using Molinspiration software [74] and
the results demonstrate that almost all the compounds meet the above mentioned criteria
making their important place in drug development.
The jointure of combinatorial chemistry and high throughput screening instigated us to
develop such molecules that can be further exploited for their pharmacological activities.
Further, different substitutions are trialled to study the structure activity relationship (SAR) of
the chalconyl blended triazole encapped silatranes.
2
.2. Chemistry
Variously substituted acetylinic chalcones have been synthesized by the most widely used
base
catalyzed
Claisen–Schmidt
reaction.
Commercially
available
o/m/p-
hydroxyacetophenones are subjected to O-alkylation with 1.2 equiv of propargyl bromide in
the presence of an excess amount of K CO (1.5 equiv) in DMF. Acetylinic acetophenones
2
3
1
/2/3 are obtained in excellent yields which then undergo aldol condensation with variedly
substituted aldehydes in the presence of methanolic NaOH resulting into acetylinic chalcones
a-4g/5a-5g/6a-6g in quite high yields. The solid chalcones are purified by recrystallization
4a-4g/5e-5g/6a-6g) while the liquid products (5a-5d) are purified by column
chromatography.
4
(
3
-azidopropyltriethoxysilane (3-AzPTES) is remodelled into its more stable and
biologically potential analogue 3-azidopropylsilatrane (3-AzPSa) by transesterification
6

ACCEPTED MANUSCRIPT
reaction with triethanolamine in toluene as solvent and presence of catalytic amount of KOH.
The alkyne terminated chalcones are then clicked onto 3-AzPSa in THF/Et N solvent system
3
at 60 °C with the catalyst loading of Cu catalyst [CuBr(PPh ) ] to incure 1,2,3-triazole bound
3
3
organosilatranes 7a-7g/8a-8g/9a-9g (Scheme 1) in excellent yields (87-93%). The melting
points and yields of the products are listed in Table 2. All the newly synthesized compounds
1
13
were characterized by IR, H and C NMR, low resolution mass spectroscopy and elemental
analysis. Compounds 7a and 7c have also been characterized by single crystal X-ray
crystallography. All the organosilatranes were synthesized under dry nitrogen atmosphere
using a vacuum glass line.
1
13
Multinuclear ( H and C) NMR spectra are very well consistent with the structure of the
synthesized compounds. Doublets around 7.23-7.52 ppm and 7.49-8.12 ppm appear in the
NMR spectra of all compounds corresponding to vinyl hydrogen atoms, α and β respectively
with a high J value of around 15 Hz confirming the (E)-configuration of the chalcones. In the
NMR spectra of acetylinic chalcones (4a-4g/5a-5g/6a-6g), alkynyl proton appears around δ ≈
2
.4 ppm that upon cyclisation with 3-AzPSa shows a shift to δ = 7.3-7.6 ppm (for 7a-7g/8a-
8
g/9a-9g) confirming the cyclisation of alkynyl moiety into triazole unit. Additionally,
shifting of -OCH protons of acetylene group from δ = 4.7 ppm to δ ≈ 5.2 ppm certifies the
2
formation of cyclised product. Also, a major shift in the protons of the carbon attached with
the azide group in 3-AzPSa from 3.2 ppm to 4.2 ppm affirms the formation of the desired
product. Further, two equivalent triplets appear around δ = 2.7-2.8 ppm and δ = 3.6-3.7 ppm
corresponding to -NCH and -OCH protons respectively of Si(OCH CH ) N skeleton.
2
2
2
2 3
Parallel shifting is scrutinized in the carbon spectrum of the respective compounds.
1
3
In C NMR spectra of all compounds, the carbonyl carbon appears as the least shielded
carbon in the region δ = 188.0-193.4 ppm. The vinyl carbons of the chalcone moiety appear
at δ = 120.7-124.4 ppm and δ = 142.1-144.9 ppm for α and β carbons respectively. Two
7

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carbons of alkynyl moiety (for 4a-4g/5a-5g/6a-6g) appear in the range of δ = 76.0-78.8 ppm
that shift around δ = 120.0-122.9 ppm and δ = 137.8-143.0 ppm in cyclised compounds (7a-
7
g/8a-8g/9a-9g), that confirms the cyclisation of alkyne functionality to triazole unit. In the
final compounds, the peaks at δ = 49.7-51.5 ppm and δ = 56.1-58.0 ppm are assigned to -
NCH and -OCH carbons of silatranyl moiety. Carbon attached to silicon appears as the most
2
2
shielded carbon at δ = 12.1-13.2 ppm clearly indicating the hypervalency in the final
compounds.
2
.3. Crystallography
Single crystals of compound 7a and 7c were grown by slow evaporation of their
corresponding solutions in chloroform at room temperature. The ORTEP plots of both the
compounds (thermal ellipsoids drawn at 50% probability) are shown in Fig. 3. Details of data
collection and structure refinement, and selected bond lengths and bond angles of both the
compounds are listed in Table 2 & 3 respectively.
Single crystal X-ray diffraction study of the compounds 7a & 7c confirms that both the
molecules crystallize in monoclinic crystal system with space group P121/c1 and C12/c1
respectively. Both the compounds possess typical silatrane structure containing Si atom
where coordination of tripodal trianionic N(CH CH O–) entities act as tetradentate
2
2
3
coordinating unit to Si and forms a penta-membered ring via a trans Si–N bond. The lattice
array for 7a favours to form a hydrophobic-hydrophilic layer arrangement along ac-plane. A
simplifier model for lattice arrangement is shown for 7a (Fig. 4) and 7c (Fig. 5). Overall
skeletal looks like a “tadpole-like” structure where the Si-bound centre resembles head region
and the chalcone-functionalized alkyl moiety resembles tail region. The tail region (~ 18 Å)
is around 8 times longer than head (~ 2.3 Å) component. The five membered chalcone moiety
is almost normal (~86 º) to functionalized alkyl part (Fig. S1). Similarly in case of compound
8

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7
c, there is an additional -OMe group at the tail region as compared to 7a. The minuscule
difference later forces compound 7c to a differently layered structure along ab-plane but less
dense type arrangement along ac-palce. Again the five-membered chalcone moiety is tilted
towards (~ 31º) one side with respect to functionalized alkyl part (Fig. S2). In both the
molecules, the central Si atom achieves a coordination number five where the O atoms of the
tripodal trianionic unit occupy equatorial positions and the N donor is present at apical site.
Among various variable structural parameters around the Si centre, the Si–N bond lengths are
2
.180(1) and 2.163(5) Å and N–Si–Cax bond angles are found to be 179.18(8), 179.51(2)° for
7
a and 7c respectively. All the Si–N bonds and angles around Si are within range of reported
values [75]. Both complexes of 7a and 7c are discrete monomer type with geometry very
close to trigonal bipyramidal (TBP) geometry around the Si atom as confirmed from the
value of τ 1.014–1.015. The distortion parameter τ = (β–α)/60 was calculated from the
structural data where the value of τ should be 0 for perfect square-pyramidal geometry and 1
for a perfect TBP structure and is applicable to five co-ordinate structures as an index of the
degree of trigonality [76]. In terms of the percentage, trigonal bipyramidal character was also
calculated by taking in account the three apical-to-equatorial bond angles and three
equatorial-to-equatorial bond angles via following equations [77]:
%
TBPax = 100*[{109.51/3(∑θn)}/(109.5–90.0)
TBPeq = 100*[{1/3(∑ϕn)– 109.5}/120.0–109.5)
%
where θn is average of angles Oeq—Si—Cax and ϕn is average of angles Oeq—Si—Oeq.
Based on the above equations, % TBPax and % TBPeq for compounds 7a and 7c are found to
be 64.82, 61.48 % and 86.57, 84.0 % respectively. Apart from the structural differences, there
are few short interactions of –CH···O/N type, present in both the compounds.
9

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2
.4. In vitro antiparasitic effect
In this study, twenty one new silatrane derivatives have been synthesized and evaluated for
their antiparasitic activities against G. lamblia and T. vaginalis. The biological assay results
against the parasites are summarized in Table 4. The antiparasitic activities of the newly
synthesized compounds were compared with the standard drug metronidazole (Met). Various
substitutions have been incorporated on the two aromatic rings of chalcones to give a number
of analogues with potential biological activities.
Firstly, we compared the activities of chalcones 7a-7g possessing p-substitution on ring A
and variedly substituted ring B against T. vaginalis and it was found that the compound 7a
with no ring substitution was less active than the substituted ones with IC = 27.24 µM.
5
0
Comparisons were made to determine if increasing the number of electron donating groups
on ring B made any difference in their activity. However, no specific trend could be
delineated on this basis. Compound 7e endowed with three –OCH groups and 7g with
3
electron withdrawing –Cl functionality were comparatively more potent than the two –OCH3
(
7d) or –CH (7f) substituted compounds. The compounds 8a-8g with o-substitution on ring
3
A showed less trichomonacidal activities as compared to the p-substituents with IC ranging
5
0
from 21.265-50.025 µM but the ring B substitution follows the same trend. On the other
hand, m-substituted chalcones 9a-9g displayed two-fold less activity than their o/p-isomers
with the IC range of 30.275-101.265 µM. Among all the tested compounds, 7e with IC =
5
0
50
1
8.245 µM demonstrated excellent efficacy against T. vaginalis (Fig. 6). This compound was
1
0

ACCEPTED MANUSCRIPT
also found to have excellent physicochemical properties, acceptable polar surface area of
1
15.67 and admirable clogP value of 3.1.
Biological assay results against G. lamblia showed that most of the compounds exhibited
comparatively low bioactivity with IC50 ranging from 19.58-131.2 µM. The compounds
substituted at o/p- position of ring A were found to be more potent than the m-substituted
compounds. Compounds with tri-methoxy substitution on ring B portrayed better activity
compared to other substitutions and compound 9e with m-position of ring A and three
methoxy groups on ring B came out as the most promising antigiardial agent with IC =
5
0
1
9.58 µM. Thus, 90% of the compounds assayed against T. vaginalis and 71% of the
compounds tested against G. lamblia were found to be more effective than the control drug
metronidazole that presented IC50 = 55.85 µM and 62.48 µM for both the parasites
respectively.
An interesting trend can be outlined from the structure activity relationship of the tested
compounds. The compounds whether with ortho, meta or para substitution at ring-A and tri-
methoxy substituent at ring-B exhibited the best giardicidal and trichomonacidal activities
among the screened compounds while the organosilatranes bearing methyl group at ring-B
were found to be less effective against both the parasites. The moieties having chlorine as the
ring-B substituent displayed intermediate activities. This may be due to the presence of bulky
methoxy groups that are responsible for the better activities of these compounds in
comparison to the unsubstituted or methyl substituted analogues. Moreover, the
physicochemical results also show better PSA values for tri-methoxy substituents supporting
its good oral bioavailability.
2
.5. In vitro cytotoxic effect
1
1

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To study the effect of compounds on mammalian cells, their toxicity was evaluated. For this,
six compounds (7e, 7f, 8a, 8d, 9b and 9e) presenting exquisite parasitic activities were
treated with Hek-293 and HeLa cells. It was evident from Table 5 that at respective 20X of
IC values none of the compounds showed any toxicity. The selectivity index (SI) of the
5
0
compounds defined as the ratio of cytotoxicity to biological activity (SI = CC Hek-293 or
50
HeLa/ IC of the parasites) was calculated. Notably all six compounds with significant in
5
0
vitro antiparasitic activity (giardicidal and trichomonacidal) possess good selectivity index.
3
3
3
. Experimental
.1. Chemistry
.1.1. Starting Material
Propargyl bromide (80% in toluene) (Sigma-Aldrich), o/m/p-hydroxyacetophenones
(
AVRA), potassium carbonate (Thomas), substituted aldehydes (Sigma-Aldrich), sodium
hydroxide (AVRA), sodium sulphate (Finar), Bromotris(triphenylphosphine)copper(I)
Sigma-Aldrich) were used as received. The organic solvents were dried according to
standard procedures. 3-azidopropylsilatrane (3-AzPSa) and acetylinic chalcones (4a-4g/5a-
(
5
g/6a-6g) were synthesized by known procedure from literature [32,78,79].
3
.1.2. Measurements
Infrared spectrum was obtained as Neat on a Thermo Scientific Fischer spectrometer.
CHN analysis was obtained on Perkin Elmer Model 2400 CHNS elemental analyser. The
1
13
NMR spectra ( H and C) were recorded on a JEOL (AL 300 MHz) and BRUKER (400
MHz) spectrometer using CDCl as internal reference and chemical shifts were reported
3
relative to tetramethylsilane. J values are given in Hz. The abbreviations used to explain
NMR are as: s, singlet; d, doublet; q, quartet; dd, doublet of doublet; t, triplet; m, multiplet.
1
2

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Mass spectral measurements (TOF MS ESþ 1.38 eV) were carried out on Waters QQ–TOF
micro Mass Spectrometer. Melting points were measured in a Mel Temp II device using
sealed capillaries and were uncorrected. Column chromatography was performed with silica
gel plates (Kieselgel 60, 230-400 mesh). Analytical thin layer chromatography was
performed employing 0.2 mm coated commercial silica gel plates (E. Merck, DC-Aluminum
sheets, Kieselgel 60 F254). Physicochemical properties of the compounds were predicted
using the Molinspiration software.
3
.1.3. General Procedure for the synthesis of 3-azidopropylsilatrane
To the stirred solution of sodium azide (5.4 g, 83.1 mmol) in dry DMF (150 ml), 5.0 g (20.7
mmol) of 3-chloropropyltriethoxysilane was added dropwise within 10 min. The reaction
mixture was stirred at 90 °C for 4 h. The removal of DMF was carried out under reduced
pressure. The crude mixture was then diluted with diethylether and filtered under inert
atmosphere. The diethyl ether was removed in vacuo and the crude oil obtained was distilled
at 130 °C under reduced pressure of 5 mm of Hg resulting into 3-AzPTES (3-
azidopropyltriethoxysilane) as colourless oil. 3-AzPTES (1 ml, 4.0 mmol) was taken in a
two-necked round bottom flask. 20 ml toluene was added to the silane followed by the
addition of triethanolamine (0.6 g, 4.0 mmol). Catalytic amount of KOH was then added to
the reaction mixture and the reaction was allowed to reflux for 4h in order to azeotropically
remove the ethanol formed during the reaction with the help of Dean-Stark assembly.
Afterwards, solvent was removed under vacuum and 15 ml hexane was added. The contents
were then left for overnight stirring followed by filtration under nitrogen and drying under
vacuum. Yield: 91 %; NMR (300 MHz, CDCl , 25 °C) δ = 0.38 (t, J = 8.1 Hz, 2H, -SiCH -),
3
H
2
1
.63 (m, 2 H, -CCH C-), 2.76 (t, J = 5.7 Hz, 6H, -NCH ), 3.18 (t, J = 6.9 Hz, 2H,
2 2
N CH CH ), 3.70 (t, J = 5.7 Hz, 6H, -OCH ).
3
2
2
2
1
3

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3
.1.4. General Procedure for the synthesis of acetylinic acetophenones (1,2,3)
o/m/p-hydroxyacetophenone (1.0 g, 7.4 mmol) was dissolved in small amount of DMF (5-10
ml) followed by the addition of anhydrous K CO (1.52 g, 11.0 mmol). The resulting
2
3
suspension was stirred for 30 min at room temperature which was then cooled to 0 °C. To
this, propargyl bromide (1.09 ml, 11.9 mmol) was subsequently added dropwise over a period
of 10 min under stirring and the resulting mixture was allowed to stir at 25 °C for 16 h. The
reaction was monitored by TLC and on consumption of starting materials, quenched by ice
cold water resulting into the formation of precipitate. The precipitate so obtained was filtered,
washed with water and recrystallized from MeOH to afford the crystalline product (1/2/3) in
excellent yield. The spectroscopic data of the resulting compounds correlate well with the
literature reports.
3
.1.5. General Procedure for the synthesis of acetylinic chalcones (4a-4g/5a-5g/6a-6g)
Methanolic NaOH (5 ml) (3% w/v) was added to a solution of the acetylenic acetophenone
/2/3 (1.0 g, 5.7 mmol) in MeOH (20 ml). The resulting mixture was stirred at 25 °C for 30
1
min followed by the addition of a methanolic solution of the commercially available
substituted aldehyde (1.0 equiv). The mixture was then stirred for 16 h at room temperature.
The reaction was monitored by TLC and on consumption of starting materials, quenched by
ice cold water resulting into the formation of precipitate (for 4a-g,5e-5g,6a-6g). The
precipitate so obtained was filtered, washed with water and recrystallized from MeOH to
afford the crystalline product. For the reactions in which no precipitation occurred (for 5a-
5
d), the product mixture was diluted with water, neutralized with 10% HCl and extracted
with ethyl acetate (20 ml) and the combined organic layers were washed twice with ice cold
water (2×20 ml). The organic layer was dried over anhydrous Na SO and the solvent was
2
4
evaporated under reduced pressure to afford yellow brown viscous oil. The crude was then
1
4

ACCEPTED MANUSCRIPT
subjected to column chromatography with EtOAc/Hexane 3:7, as eluent. The spectroscopic
data of the chalcones correlate well with the literature reports.
3
.1.6. General Procedure for the synthesis of chalconyl silatranes (7a-7g/8a-8g/9a-9g)
To the stirred solution of acetylinic chalcones (4a-4g/5a-5g/6a-6g) in THF/Et N solvent
3
system, taken in a two necked round bottomed flask, was added catalytic amount of
Bromotris(triphenylphosphine)copper(I) (0.01 mmol/alkyne function) followed by the
addition of 3-AzPSa. The reaction mixture was then refluxed at 60 °C for 4 h. Thereafter, the
solvent was evaporated under vacuum and on slow addition of hexane (10 ml), solid
precipitated out. The solid so obtained was left for overnight stirring and then filtered under
nitrogen and dried under vacuum resulting into desired organosilatranes 7a-7g/8a-8g/9a-9g in
excellent yields.
3
.1.6.1. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-
phenylprop-2-en-1-one (7a)
The quantities used were as 4a (1.0 g, 3.8 mmol), 3-AzPSa (0.98 g, 3.8 mmol). Yellow solid,
-1
Yield: 1.82 g, 3.5 mmol, 92 %. IR (neat, cm ): 563 (N→Si), 758, 1087 (Si-O), 1648 (C=O),
1
2
941 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.35 (m, 2H, -SiCH -), 1.95 (m, 2H, -
3
2
CCH C-), 2.75 (t, J = 5.8 Hz, 6H, -CH N-), 3.70 (t, J = 5.8 Hz, 6H, -OCH CH -), 4.30 (t, J =
2
2
2
2
7
4
.4 Hz, 2H, -N CH -), 5.26 (s, 2H, -OCH -), 7.04 (d, J = 8.9 Hz, 2H, H2, H6), 7.30-7.37 (m,
3 2 2
H, Tz-H, H9-H11), 7.49 (d, J = 15.6 Hz, 1H, Hα), 7.60 (d, J = 8.3 Hz, 2H, H8, H12), 7.74
13
(
d, J = 15.6 Hz, 1H, Hβ), 7.99 (d, J = 8.9 Hz, 2H, H3, H5). C NMR (75 MHz, CDCl , 25
3
°
C): δ 13.0 (SiCH ), 26.3 (CCH C), 51.3 (CH CH N), 53.4 (N CH ), 57.7 (OCH CH ), 62.5
2 2 2 2 3 2 2 2
(
OCH ), 115.0 (C2, C6), 122.1, 143.0 (Tz-C), 122.7 (Cα), 128.6 (C8, C12), 129.1 (C10),
2
1
30.4 (C9, C11), 131.0 (C4), 131.7 (C3, C5), 135.5 (C7), 144.0 (Cβ), 162.4 (C1), 188.1
(C=O). MS: m/z (relative abundance (%)): 543 (53), 521 (76), 246 (32), 214 (31), 167 (36),
1
5

ACCEPTED MANUSCRIPT
1
6
58 (89), 149 (100). Anal. Calcd. for C H N O Si: C, 62.29; H, 6.19; N, 10.76. Found: C,
2
7
32
4
5
2.15; H, 6.18; N, 10.63.
3
.1.6.2. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(4-
methoxyphenyl)prop-2-en-1-one (7b)
The quantities used were as 4b (1.0 g, 3.4 mmol), 3-AzPSa (0.88 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.68 g, 3.1 mmol, 90 %. IR (neat, cm ): 580 (N→Si), 771, 1028 (Si-O), 1658 (C=N),
1
2
945 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.29 (m, 2H, -SiCH -), 1.89 (m, 2H, -
3
2
CCH C-), 2.70 (t, J = 5.8 Hz, 6H, -CH N-), 3.64 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.79 (s, 3H,
2
2
2
2
-
OCH ), 4.26 (t, J = 7.4 Hz, 2H, -N CH -), 5.22 (s, 2H, -OCH -), 6.83 (d, J = 8.6 Hz, 2H, H9,
3 3 2 2
H11), 6.98 (d, J = 8.7 Hz, 2H, H2, H6), 7.32 (d, J = 15.5 Hz, 1H, Hα), 7.50 (d, J = 8.6 Hz,
H, H8, H12), 7.56 (s, 1H, Tz-H), 7.66 (d, J = 15.5 Hz, 1H, Hβ), 7.93 (d, J = 8.7 Hz, 2H, H3,
2
1
3
H5). C NMR (75 MHz, CDCl , 25 °C): δ 13.2 (SiCH ), 26.5 (CCH C), 51.5 (CH CH N),
3
2
2
2
2
5
3.7 (N CH ), 55.8 (OCH ), 58.0 (OCH CH ), 62.7 (OCH ), 111.6 (C9, C11), 115.1 (C2,
3 2 3 2 2 2
C6), 121.2, 140.0 (Tz-C), 123.2 (Cα), 129.7 (C8, C12), 131.2 (C7), 131.8 (C4), 132.3 (C3,
C5), 142.3 (Cβ), 159.2 (C10), 162.4 (C1), 189.4 (C=O). MS: m/z (relative abundance (%)):
5
73 (38), 551 (100). Anal. Calcd. for C H N O Si: C, 61.07; H, 6.22; N, 10.17. Found: C,
28 34 4 6
6
0.98; H, 6.21; N, 10.12.
3
.1.6.3. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2-
methoxyphenyl)prop-2-en-1-one (7c)
The quantities used were as 4c (1.0 g, 3.4 mmol), 3-AzPSa (0.88 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.67 g, 3.1 mmol, 89 %. IR (neat, cm ): 586 (N→Si), 752, 1053 (Si-O), 1646 (C=N),
1
2
946 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.30 (m, 2H, -SiCH -), 1.90 (m, 2H, -
3
2
CCH C-), 2.71 (t, J = 5.8 Hz, 6H, -CH N-), 3.65 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.86 (s, 3H,
2
2
2
2
-
OCH ), 4.26 (t, J = 7.3 Hz, 2H, -N CH -), 5.21 (s, 2H, -OCH -), 6.83-6.92 (m, 2H, H9,
3 3 2 2
1
6

ACCEPTED MANUSCRIPT
H11), 6.99 (d, J = 8.8 Hz, 2H, H2, H6), 7.27 (t, J = 7.0 Hz, 1H, H10), 7.50-7.57 (m, 3H, Hα,
1
3
H8, Tz-H), 7.92-8.00 (m, 3H, Hβ, H3, H5). C NMR (75 MHz, CDCl , 25 °C): δ 12.9
3
(
SiCH ), 26.2 (CCH C), 51.2 (CH CH N), 53.4 (N CH ), 55.5 (OCH ), 57.6 (OCH CH ),
2 2 2 2 3 2 3 2 2
6
1
1
2.4 (OCH ), 111.2 (C11), 114.8 (C2, C6), 120.9 (C7), 122.9, 139.6 (Tz-C), 124.4 (Cα),
2
25.7 (C9), 129.4 (C8), 130.9 (C10), 131.5 (C4), 132.0 (C3, C5), 144.1 (Cβ), 158.9 (C12),
62.1 (C1), 189.1 (C=O). MS: m/z (relative abundance (%)): 573 (100), 551 (40), 150 (15).
Anal. Calcd. for C H N O Si: C, 61.07; H, 6.22; N, 10.17. Found: C, 60.93; H, 6.19; N,
2
8
34
4
6
1
0.09.
3
.1.6.4. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2,4-
dimethoxyphenyl)prop-2-en-1-one (7d)
The quantities used were as 4d (1.0 g, 3.1 mmol), 3-AzPSa (0.80 g, 3.1 mmol). Yellow solid,
-1
Yield: 1.63 g, 2.8 mmol, 91 %. IR (neat, cm ): 579 (N→Si), 764, 1095 (Si-O), 1651 (C=N),
1
2
929 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.30 (m, 2H, -SiCH -), 1.90 (m, 2H, -
3
2
CCH C-), 2.71 (t, J = 5.3 Hz, 6H, -CH N-), 3.65 (t, J = 5.3 Hz, 6H, -OCH CH -), 3.85 (s, 3H,
2
2
2
2
-OCH ), 3.78 (s, 3H, -OCH ), 4.26 (t, J = 7.5 Hz, 2H, -N CH -), 5.21 (s, 2H, -OCH -), 6.37
3 3 3 2 2
(s, 1H, H11), 6.43 (d, J = 7.5 Hz, 1H, H9), 6.98 (d, J = 7.2 Hz, 2H, H2, H6), 7.14 (d, J = 7.5
Hz, 1H, H8), 7.43 (d, J = 15.5 Hz, 1H, Hα), 7.57 (s, 1H, Tz-H), 7.88-7.93 (m, 3H, Hβ, H3,
1
3
H5). C NMR (75 MHz, CDCl , 25 °C): δ 12.8 (SiCH ), 26.0 (CCH C), 50.8 (CH CH N),
3
2
2
2
2
5
3.1 (N CH ), 55.1 (OCH ), 55.2 (OCH ), 57.3 (OCH CH ), 62.0 (OCH ), 98.3 (C11), 105.2
3 2 3 3 2 2 2
(
C9), 114.4 (C7), 117.2 (C2, C6), 120.0, 139.4 (Tz-C), 122.6 (Cα), 128.2 (C8), 130.5 (C4),
31.9 (C3, C5), 142.7 (Cβ), 160.2 (C12), 161.7 (C10), 162.8 (C1), 188.7 (C=O). MS: m/z
relative abundance (%)): 603 (32), 581 (100). Anal. Calcd. for C H N O Si: C, 59.98; H,
1
(
2
9
36
4
7
6
.25; N, 9.65. Found: C, 59.83; H, 6.15; N, 9.58.
1
7

ACCEPTED MANUSCRIPT
3
.1.6.5. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2,3,4-
trimethoxyphenyl)prop-2-en-1-one (7e)
The quantities used were as 4e (1.0 g, 2.8 mmol), 3-AzPSa (0.72 g, 2.8 mmol). Yellow solid,
-1
Yield: 1.53 g, 2.5 mmol, 90 %. IR (neat, cm ): 580 (N→Si), 761, 1091 (Si-O), 1652 (C=N),
1
2
933 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.29 (m, 2H, -SiCH -), 1.89 (m, 2H, -
3
2
CCH C-), 2.70 (t, J = 5.8 Hz, 6H, -CH N-), 3.64 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.80 (s, 3H,
2
2
2
2
-
OCH ), 3.84 (s, 3H, -OCH ), 3.88 (s, 3H, -OCH ), 4.25 (t, J = 7.4 Hz, 2H, -N CH -), 5.21 (s,
3 3 3 3 2
2
H, -OCH -), 6.60 (d, J = 8.8 Hz, 1H, H9), 6.98 (d, J = 8.8 Hz, 2H, H2, H6), 7.26 (d, J = 8.8
2
Hz, 1H, H8), 7.45 (d, J = 15.7 Hz, 1H, Hα), 7.56 (s, 1H, Tz-H), 7.83 (d, J = 15.7 Hz, 1H,
1
3
Hβ), 7.92 ( d, J = 8.8 Hz, 2H, H3, H5). C NMR (75 MHz, CDCl , 25 °C): δ 12.9 (SiCH ),
3
2
2
6.2 (CCH C), 51.1 (CH CH N), 53.3 (N CH ), 56.0 (OCH ), 57.5 (OCH CH ), 60.7
2 2 2 3 2 3 2 2
(
OCH ), 61.3 (OCH ), 62.3 (OCH ), 107.8 (C7, C9), 114.7 (C2, C6), 121.2 (C8), 122.8,
3 3 2
1
1
39.2 (Tz-C), 123.8 (Cα), 128.4 (C4), 130.8 (C3, C5), 139.2 (C11), 142.8 (Cβ), 154.0 (C12),
55.8 (C10), 162.1 (C1), 188.5 (C=O). MS: m/z (relative abundance (%)): 633 (100), 611
(
38). Anal. Calcd. for C H N O Si: C, 59.00; H, 6.27; N, 9.17. Found: C, 58.89; H, 6.18; N,
30 38 4 8
9
.11.
3
.1.6.6. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-p-tolyl-
prop-2-en-1-one (7f)
The quantities used were as 4f (1.0 g, 3.6 mmol), 3-AzPSa (0.93 g, 3.6 mmol). Yellow solid,
-1
Yield: 1.73 g, 3.2 mmol, 90 %. IR (neat, cm ): 576 (N→Si), 756, 1094 (Si-O), 1659 (C=N),
1
2
9437 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.30 (m, 2H, -SiCH -), 1.90 (m, 2H, -
3
2
CCH C-), 2.33 (s, 3H, -CH ), 2.71 (t, J = 5.8 Hz, 6H, -CH N-), 3.65 (t, J = 5.8 Hz, 6H, -
2
3
2
OCH CH -), 4.26 (t, J = 7.4 Hz, 2H, -N CH -), 5.21 (s, 2H, -OCH -), 6.99 (d, J = 8.8 Hz, 2H,
2
2
3
2
2
H2, H6), 7.13 (d, J = 8.0 Hz, 2H, H9, H11), 7.23 (d, J = 15.6 Hz, 1H, Hα), 7.45 (d, J = 8.0
Hz, 2H, H8, H12), 7.57 (s, 1H, Tz-H), 7.67 (d, J = 15.6 Hz, 1H, Hβ), 7.94 (d, J = 8.8 Hz, 2H,
1
8

ACCEPTED MANUSCRIPT
13
H3, H5). C NMR (75 MHz, CDCl , 25 °C): δ 12.9 (SiCH ), 21.5 (CH ), 26.2 (CCH C),
3
2
3
2
5
1.1 (CH CH N), 53.3 (N CH ), 57.6 (OCH CH ), 62.4 (OCH ), 114.8 (C2, C6), 121.0,
2 2 3 2 2 2 2
1
42.8 (Tz-C), 122.8 (Cα), 128.4 (C8, C12), 128.5 (C4), 129.8 (C9, C11), 130.9 (C7), 131.7
(C3, C5), 140.6 (C10), 144.1 (Cβ), 162.2 (C1), 188.4 (C=O). MS: m/z (relative abundance
(
%)): 557 (34), 535 (100). Anal. Calcd. for C H N O Si: C, 62.90; H, 6.41; N, 10.48.
2
8
34
4
5
Found: C, 62.87; H, 6.35; N, 10.43.
3
.1.6.7. (E)-1-(4-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(4-
chlorophenyl)prop-2-en-1-one (7g)
The quantities used were as 4g (1.0 g, 3.4 mmol), 3-AzPSa (0.87 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.64 g, 3.0 mmol, 88 %. IR (neat, cm ): 571 (N→Si), 761, 1085 (Si-O), 1655 (C=N),
1
2
925 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.29 (m, 2H, -SiCH -), 1.90 (m, 2H, -
3
2
CCH C-), 2.71 (t, J = 5.8 Hz, 6H, -CH N-), 3.64 (t, J = 5.8 Hz, 6H, -OCH CH -), 4.25 (t, J =
2
2
2
2
7
8
.4 Hz, 2H, -N CH -), 5.21 (s, 2H, -OCH -), 7.00 (d, J = 8.8 Hz, 2H, H2, H6), 7.30 (d, J =
3 2 2
.5 Hz, 2H, H9, H11), 7.42 (d, J = 15.6 Hz, 1H, Hα), 7.50 (d, J = 8.5 Hz, 2H, H8, H12), 7.57
1
3
(
s, 1H, Tz-H), 7.63 (d, J = 15.6 Hz, 1H, Hβ), 7.93 (d, J = 8.8 Hz, 2H, H3, H5). C NMR (75
MHz, CDCl , 25 °C): δ 12.9 (SiCH ), 26.2 (CCH C), 51.2 (CH CH N), 53.4 (N CH ), 57.6
3
2
2
2
2
3
2
(
OCH CH ), 62.4 (OCH ), 114.9 (C2, C6), 122.5, 142.5 (Tz-C), 122.7 (Cα), 129.4 (C8, C12),
2 2 2
1
29.6 (C9, C11), 131.0 (C4), 131.4 (C3, C5), 133.4 (C7), 133.7 (C10), 142.9 (Cβ), 162.6
(C1), 188.0 (C=O). MS: m/z (relative abundance (%)): 577 (23), 555 (100). Anal. Calcd. for
C H ClN O Si: C, 58.42; H, 5.63; N, 10.09. Found: C, 58.38; H, 5.56; N, 9.89.
27
31
4
5
3
.1.6.8. (E)-1-(2-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-
phenylprop-2-en-1-one (8a)
The quantities used were as 5a (1.0 g, 3.8 mmol), 3-AzPSa (0.98 g, 3.8 mmol). Yellow solid,
-1
Yield: 1.70 g, 3.3 mmol, 88 %. IR (neat, cm ): 558 (N→Si), 755, 1094 (Si-O), 1660 (C=N),
1
9

ACCEPTED MANUSCRIPT
1
2
931 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.19 (m, 2H, -SiCH -), 1.73 (m, 2H, -
3 2
CCH C-), 2.68 (t, J = 5.7 Hz, 6H, -CH N-), 3.61 (t, J = 5.7 Hz, 6H, -OCH CH -), 3.99 (t, J =
2
2
2
2
7
1
.2 Hz, 2H, -N CH -), 5.21 (s, 2H, -OCH -), 6.97 (t, J = 7.5 Hz, 1H, H2), 7.06 (d, J = 7.6 Hz,
3 2 2
H, H4), 7.19-7.31 (m, 5H, H8-H12), 7.36-7.40 (m, 2H, H3, Hα), 7.41 (s, 1H, Tz-H), 7.49 (d,
1
3
J = 15.9 Hz, 1H, Hβ), 7.59 (d, J = 7.6 Hz, 1H, H5). C NMR (75 MHz, CDCl , 25 °C): δ
3
1
2.8 (SiCH ), 26.1 (CCH C), 51.1 (CH CH N), 53.1 (N CH ), 57.6 (OCH CH ), 63.1
2 2 2 2 3 2 2 2
(
OCH ), 113.1 (C2), 121.4, 142.4 (Tz-C), 122.7 (C4, C6), 123.9 (Cα), 127.6 (C8, C12), 128.5
2
(C10), 129.0 (C9, C11), 131.0 (C5), 133.2 (C7), 135.3 (C3), 142.9 (Cβ), 157.3 (C1), 192.0
(
C=O). Anal. Calcd. for C H N O Si: C, 62.29; H, 6.19; N, 10.76. Found: C, 62.25; H,
27
32
4
5
6
.16; N, 10.62.
3
.1.6.9. (E)-1-(2-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(4-
methoxyphenyl)prop-2-en-1-one (8b)
The quantities used were as 4a (1.0 g, 3.4 mmol), 3-AzPSa (0.88 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.65 g, 3.0 mmol, 86 %. IR (neat, cm ): 558 (N→Si), 755, 1094 (Si-O), 1660 (C=N),
1
2
930 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.20 (m, 2H, -SiCH -), 1.75 (m, 2H, -
3
2
CCH C-), 2.67 (t, J = 5.7 Hz, 6H, -CH N-), 3.60 (t, J = 5.7 Hz, 6H, -OCH CH -), 3.76 (s, 3H,
2
2
2
2
-
OCH ), 4.04 (t, J = 7.2 Hz, 2H, -N CH -), 5.20 (s, 2H, -OCH -), 6.79 (d, J = 8.5 Hz, 2H, H9,
3 3 2 2
H11), 6.93-7.06 (m, 2H, H2, H4), 7.22 (d, J = 8.5 Hz, 2H, H8, H12), 7.33-7.44 (m, 2H, H3,
1
3
Hα), 7.47 (s, 1H, Tz-H), 7.57 (d, J = 14.8 Hz, 1H, Hβ), 7.73 (d, J = 8.3 Hz, 1H, H5). C
NMR (75 MHz, CDCl , 25 °C): δ 12.8 (SiCH ), 26.1 (CCH C), 51.2 (CH CH N), 53.2
3
2
2
2
2
(N CH ), 55.2 (OCH ), 57.7 (OCH CH ), 63.1 (OCH ), 113.1 (C9, C11), 113.6 (C2), 114.6
3 2 3 2 2 2
(
C6), 120.3, 142.5 (Tz-C), 121.5 (Cα), 124.9 (C4), 125.5 (C8, C12), 128.1 (C7), 130.3 (C5),
33.0 (C3), 143.2 (Cβ), 157.3 (C10), 161.6 (C1), 191.9 (C=O). Anal. Calcd. for
C H N O Si: C, 61.07; H, 6.22; N, 10.17. Found: C, 60.97; H, 6.12; N, 10.13.
1
28
34
4
6
2
0

ACCEPTED MANUSCRIPT
3
.1.6.10. (E)-1-(2-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2-
methoxyphenyl)prop-2-en-1-one (8c)
The quantities used were as 5c (1.0 g, 3.4 mmol), 3-AzPSa (0.88 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.65 g, 3.0 mmol, 88 %. IR (neat, cm ): 586 (N→Si), 749, 1095 (Si-O), 1654 (C=N),
1
2
929 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.21 (m, 2H, -SiCH -), 1.74 (m, 2H, -
3
2
CCH C-), 2.70 (t, J = 5.7 Hz, 6H, -CH N-), 3.64 (t, J = 5.7 Hz, 6H, -OCH CH -), 3.79 (s, 3H,
2
2
2
2
-
OCH ), 3.99 (t, J = 7.2 Hz, 2H, -N CH -), 5.24 (s, 2H, -OCH -), 6.80-6.89 (m, 2H, H9,
3 3 2 2
H11), 6.98-7.09 (m, 2H, H2, H4), 7.19-7.29 (m, 2H, H8, H10), 7.37-7.44 (m, 2H, H3, Hα),
13
7
.58 (s, 1H, Tz-H), 7.80-7.89 (m, 2H, Hβ, H5). C NMR (75 MHz, CDCl , 25 °C): δ 12.8
3
(
SiCH ), 26.1 (CCH C), 51.1 (CH CH N), 53.0 (N CH ), 55.3 (OCH ), 57.5 (OCH CH ),
2 2 2 2 3 2 3 2 2
6
1
3.3 (OCH ), 111.1 (C11), 113.1 (C2, C7), 121.0 (C9), 121.4 (C4, C6), 122.6, 137.8 (Tz-C),
2
24.3 (Cα), 128.1 (C8), 128.9 (C10), 130.9 (C5), 132.9 (C3), 143.1 (Cβ), 157.2 (C12), 158.7
(
C1), 192.3 (C=O). Anal. Calcd. for C H N O Si: C, 61.07; H, 6.22; N, 10.17. Found: C,
28 34 4 6
6
0.96; H, 6.12; N, 10.13.
3
.1.6.11. (E)-1-(2-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2,4-
dimethoxyphenyl)prop-2-en-1-one (8d)
The quantities used were as 5d (1.0 g, 3.1 mmol), 3-AzPSa (0.80 g, 3.1 mmol). Yellow solid,
-1
Yield: 1.64 g, 2.8 mmol, 91 %. IR (neat, cm ): 579 (N→Si), 755, 1096 (Si-O), 1638 (C=N),
1
2
925 (C=C-H). H NMR (400 MHz, CDCl , 25 °C): δ 0.33 (m, 2H, -SiCH -), 1.87 (m, 2H, -
3
2
CCH C-), 2.78 (t, J = 5.8 Hz, 6H, -CH N-), 3.71 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.80 (s, 3H,
2
2
2
2
-OCH ), 3.83 (s, 3H, -OCH ), 4.13 (t, J = 7.2 Hz, 2H, -N CH -), 5.28 (s, 2H, -OCH -), 6.44
3 3 3 2 2
(s, 1H, H11), 6.50 (d, J = 8.6 Hz, 1H, H9), 7.05 (t, J = 7.5 Hz, 1H, H4), 7.13 (d, J = 8.0 Hz,
1
7
H, H2), 7.34-7.47 (m, 3H, H8, Hα, H3), 7.54 (s, 1H, Tz-H), 7.62 (d, J = 7.6 Hz, 1H, H5),
1
3
.87 (d, J = 16.0 Hz, 1H, Hβ). C NMR (101 MHz, CDCl , 25 °C): δ 13.1 (SiCH ), 26.3
3
2
(
CCH C), 51.0 (CH CH N), 53.3 (N CH ), 55.5 (2×OCH ), 57.5 (OCH CH ), 63.3 (OCH ),
2 2 2 3 2 3 2 2 2
2
1

ACCEPTED MANUSCRIPT
9
1
8.4 (C11), 105.4 (C9), 113.1 (C7), 117.1 (C2), 121.3, 138.6 (Tz-C), 122.7 (Cα), 125.5 (C6),
28.3 (C6), 130.2 (C8), 130.4 (C5), 132.5 (C3), 143.4 (Cβ), 156.8 (C12), 160.1 (C10), 162.9
(
C1), 193.4 (C=O). Anal. Calcd. for C H N O Si: C, 59.98; H, 6.25; N, 9.65. Found: C,
29 36 4 7
5
9.86; H, 6.13; N, 9.56.
3
.1.6.12. (E)-1-(2-((1-(3-(triethoxysilatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-
(2,3,4-trimethoxyphenyl)prop-2-en-1-one (8e)
The quantities used were as 5e (1.0 g, 2.8 mmol), 3-AzPSa (0.72 g, 2.8 mmol). Yellow solid,
Yield: 1.51 g, 2.5 mmol, 89 %. IR: 574 (N→Si), 758, 1096 (Si-O), 1641 (C=N), 2927 (C=C-
1
H). H NMR (400 MHz, CDCl , 25 °C): δ 0.33 (m, 2H, -SiCH -), 1.88 (m, 2H, -CCH C-),
3
2
2
2
.77 (t, J = 5.8 Hz, 6H, -CH N-), 3.71 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.86 (m, 9H, 3×-
2 2 2
OCH ), 4.18 (t, J = 7.2 Hz, 2H, -N CH -), 5.28 (s, 2H, -OCH -), 6.68 (d, J = 8.5 Hz, 1H, H9),
3
3
2
2
7
.04 (t, J = 7.5 Hz, 1H, H4), 7.12 (d, J = 8.5 Hz, 1H, H8), 7.20 (d, J = 8.8 Hz, 1H, H2), 7.36
(d, J = 16.0 Hz, 1H, Hα), 7.43-7.46 (m, 1H, H3), 7.56 (s, 1H, Tz-H), 7.63 (d, J = 7.5 Hz, 1H,
1
3
H5), 7.82 (d, J = 16.0 Hz, 1H, Hβ). C NMR (101 MHz, CDCl , 25 °C): δ 12.1 (SiCH ),
3
2
2
5.2 (CCH C), 49.9 (CH CH N), 52.3 (N CH ), 55.1 (OCH ), 56.5 (OCH CH ), 59.9
2 2 2 3 2 3 2 2
(
OCH ), 60.5 (OCH ), 62.0 (OCH ), 106.7 (C9), 108.4 (C7), 112.1 (C2), 120.3 (C6), 121.0,
3 3 2
1
41.3 (Tz-C), 121.8 (Cα), 122.1 (C4), 125.2 (C8), 129.5 (C5), 131.7 (C3), 137.0 (C11), 142.1
(
Cβ), 152.6 (C12), 154.6 (C10), 155.8 (C1), 191.9 (C=O). Anal. Calcd. for C H N O Si: C,
30 38 4 8
5
9.00; H, 6.27; N, 9.17. Found: C, 58.94; H, 6.23; N, 9.18.
3
.1.6.13. (E)-1-(2-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-p-tolyl-
prop-2-en-1-one (8f)
The quantities used were as 5f (1.0 g, 3.6 mmol), 3-AzPSa (0.93 g, 3.6 mmol). Yellow solid,
-1
Yield: 1.67 g, 3.1 mmol, 87 %. IR (neat, cm ): 576 (N→Si), 756, 1094 (Si-O), 1660 (C=N),
1
2
933 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.22 (m, 2H, -SiCH -), 1.75 (m, 2H, -
3
2
2
2

ACCEPTED MANUSCRIPT
CCH C-), 2.33 (s, 3H, -CH ), 2.71 (t, J = 5.8 Hz, 6H, -CH N-), 3.64 (t, J = 5.8 Hz, 6H, -
2
3
2
OCH CH -), 4.01 (t, J = 7.2 Hz, 2H, -N CH -), 5.23 (s, 2H, -OCH -), 6.99 (t, J = 7.5 Hz, H4),
2
2
3
2
2
7
.06-7.12 (m, 3H, H2, H9, H11), 7.31 (d, J = 6.6 Hz, 2H, H8, H12), 7.37-7.40 (m, 2H, H3,
1
3
Hα), 7.42 (s, 1H, Tz-H), 7.49 (d, J = 15.9 Hz, 1H, Hβ), 7.59 (d, J = 7.5 Hz, 1H, H5). C
NMR (75 MHz, CDCl , 25 °C): δ 12.9 (SiCH ), 21.4 (OCH ), 26.1 (CCH C), 50.9
3
2
3
2
(
CH CH N), 53.2 (N CH ), 57.5 (OCH CH ), 63.0 (OCH ), 113.1 (C2), 121.3, 140.8 (Tz-C),
2 2 3 2 2 2 2
1
21.4 (C4), 122.8 (Cα), 126.5 (C8, C12), 128.5 (C9, C11), 129.7 (C5), 130.6 (C3), 132.3
(
C7), 133.1 (C10), 142.9 (Cβ), 157.1 (C1), 192.8 (C=O). Anal. Calcd. for C H N O Si: C,
28 34 4 5
6
2.90; H, 6.41; N, 10.48. Found: C, 62.83; H, 6.38; N, 10.34.
3
.1.6.14. (E)-1-(2-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(4-
chlorophenyl)prop-2-en-1-one (8g)
The quantities used were as 5g (1.0 g, 3.4 mmol), 3-AzPSa (0.87 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.62 g, 2.9 mmol, 87 %. IR (neat, cm ): 583 (N→Si), 757, 1097 (Si-O), 1667 (C=N),
1
2
923 (C=C-H). H NMR (300 MHz, CDCl , 25 °C): δ 0.29 (m, 2H, -SiCH -), 1.90 (m, 2H, -
3
2
CCH C-), 2.71 (t, J = 5.8 Hz, 6H, -CH N-), 3.65 (t, J = 5.8 Hz, 6H, -OCH CH -), 4.25 (t, J =
2
2
2
2
7
1
.2 Hz, 2H, -N CH -), 5.21 (s, 2H, -OCH -), 7.08 (t, J = 7.4 Hz, 1H, H4), 7.14 (d, J = 8.3 Hz,
3 2 2
H, H2), 7.35 (d, J = 8.3 Hz, 2H, H9, H11), 7.40 (s, 1H, Tz-H), 7.43 (d, J = 8.0 Hz, 2H, H8,
H12), 7.48-7.50 (m, 2H, Hα, H3), 7.54 (d, J = 15.9 Hz, 1H, Hβ), 7.60 (d, J = 7.3 Hz, 1H,
1
3
H5). C NMR (75 MHz, CDCl , 25 °C): δ 13.6 (SiCH ), 26.5 (CCH C), 50.1 (CH CH N),
3
2
2
2
2
5
1
2.7 (N CH ), 56.7 (OCH CH ), 61.4 (OCH ), 114.2 (C2), 121.0, 138.9 (Tz-C), 122.6 (Cα),
3 2 2 2 2
23.9 (C4), 128.0 (C8, C12), 128.7 (C9, C11), 129.6 (C5), 130.1 (C7), 133.4 (C10), 135.2
(
C3), 142.4 (Cβ), 158.3 (C1), 188.6 (C=O). Anal. Calcd. for C H ClN O Si: C, 58.42; H,
27 31 4 5
5
.63; N, 10.09. Found: C, 58.37; H, 5.63; N, 10.02.
2
3

ACCEPTED MANUSCRIPT
3
.1.6.15. (E)-1-(3-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-
phenylprop-2-en-1-one (9a)
The quantities used were as 6a (1.0 g, 3.8 mmol), 3-AzPSa (0.98 g, 3.8 mmol). Yellow solid,
-1
Yield: 1.84 g, 3.5 mmol, 93 %. Yellow solid: 0.95 g, Yield: 93 %. IR (neat, cm ): 580
1
(
N→Si), 771, 1028 (Si-O), 1658 (C=N), 2945 (C=C-H). H NMR (400 MHz, CDCl , 25 °C):
3
δ 0.42 (m, 2H, -SiCH -), 2.00 (m, 2H, -CCH C-), 2.80 (t, J = 5.8 Hz, 6H, -CH N-), 3.75 (t, J
2
2
2
=
5.8 Hz, 6H, -OCH CH -), 4.34 (t, J = 7.5 Hz, 2H, -N CH -), 5.26 (s, 2H, -OCH -), 7.22 (d,
2 2 3 2 2
J = 8.2 Hz, 1H, H2), 7.35 (s, 1H, Tz-H), 7.40-7.44 (m, 3H, H9-H11), 7.52 (d, J = 15.7 Hz,
1
H, Hα), 7.62 (d, J = 7.7 Hz, 1H, H4), 7.63-7.67 (m, 3H, H7, H8, H12), 7.68 (s, 1H, H6),
1
3
7
.81 (d, J = 15.7 Hz, 1H, Hβ). C NMR (101 MHz, CDCl , 25 °C): δ 13.2 (SiCH ), 26.3
3
2
(
CCH C), 51.0 (CH CH N), 53.4 (N CH ), 57.5 (OCH CH ), 62.3 (OCH ), 114.5 (C6),
2 2 2 3 2 2 2 2
1
19.6 (C2), 121.3, 143.0 (Tz-C), 122.2 (Cα), 122.9 (C4), 128.5 (C8, C12), 129.0 (C10), 129.7
(C9, C11), 130.5 (C3), 134.9 (C7), 139.6 (C5), 144.9 (Cβ), 158.7 (C1), 190.2 (C=O). Anal.
Calcd. for C H N O Si: C, 62.29; H, 6.19; N, 10.76. Found: C, 62.23; H, 6.13; N, 10.68.
2
7
32
4
5
3
.1.6.16. (E)-1-(3-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(4-
methoxyphenyl)prop-2-en-1-one (9b)
The quantities used were as 6b (1.0 g, 3.4 mmol), 3-AzPSa (0.88 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.71 g, 3.1 mmol, 91 %. IR (neat, cm ): 573 (N→Si), 753, 1086 (Si-O), 1660 (C=N),
1
2
933 (C=C-H). H NMR (400 MHz, CDCl , 25 °C): δ 0.32 (m, 2H, -SiCH -), 1.96 (m, 2H, -
3
2
CCH C-), 2.83 (t, J = 5.8 Hz, 6H, -CH N-), 3.73 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.86 (s, 3H,
2
2
2
2
-
OCH ), 4.32 (t, J = 7.3 Hz, 2H, -N CH -), 5.23 (s, 2H, -OCH -), 6.95 (d, J = 8.7 Hz, 2H, H9,
3 3 2 2
H11), 7.23 (d, J = 8.2 Hz, 1H, H2), 7.34 (s, 1H, H6), 7.44 (s, 1H, Tz-H), 7.48 (d, J = 15.6 Hz,
1
3
1
H, Hα), 7.62-7.68 (m, 4H, H3, H4, H8, H12), 7.79 (d, J = 15.6 Hz, 1H, Hβ). C NMR (101
MHz, CDCl , 25 °C): δ 12.5 (SiCH ), 25.5 (CCH C), 49.7 (CH CH N), 52.2 (N CH ), 54.4
3
2
2
2
2
3
2
(
OCH ), 56.3 (OCH CH ), 60.9 (OCH ), 113.2 (C6), 113.4 (C9, C11), 118.4 (C2), 118.6
3 2 2 2
2
4

ACCEPTED MANUSCRIPT
(C4), 120.1, 141.6 (Tz-C), 122.4 (Cα), 126.4 (C8, C12), 128.7 (C7), 129.4 (C3), 138.7 (C5),
1
43.5 (Cβ), 157.5 (C10), 160.7 (C1), 188.6 (C=O). Anal. Calcd. for C H N O Si: C, 61.07;
28 34 4 6
H, 6.22; N, 10.17. Found: C, 61.04; H, 6.13; N, 10.07.
3
.1.6.17. (E)-1-(3-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2-
methoxyphenyl)prop-2-en-1-one (9c)
The quantities used were as 6c (1.0 g, 3.4 mmol), 3-AzPSa (0.88 g, 3.4 mmol). Yellow solid,
-1
Yield: 1.69 g, 3.1 mmol, 90 %. IR (neat, cm ): 585 (N→Si), 766, 1095 (Si-O), 1654 (C=N),
1
2
921 (C=C-H). H NMR (400 MHz, CDCl , 25 °C): δ 0.42 (m, 2H, -SiCH -), 2.00 (m, 2H, -
3
2
CCH C-), 2.80 (t, J = 5.8 Hz, 6H, -CH N-), 3.75 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.92 (s, 3H,
2
2
2
2
-
OCH ), 4.34 (t, J = 7.5 Hz, 2H, -N CH -), 5.26 (s, 2H, -OCH -), 6.94 (d, J = 8.3 Hz, 1H,
3 3 2 2
H11), 7.00 (t, J = 7.5 Hz, 1H, H9), 7.21 (d, J = 6.5 Hz, 1H, H2), 7.36-7.43 (m, 3H, Hα, H8,
H10), 7.58 (s, 1H, Tz-H), 7.61-7.66 (m, 2H, H3, H4), 7.69 (s, 1H, H6), 8.12 (d, J = 15.9 Hz,
1
3
1
H, Hβ). C NMR (101 MHz, CDCl , 25 °C): δ 13.2 (SiCH ), 26.3 (CCH C), 51.0
3 2 2
(
CH CH N), 53.4 (N CH ), 55.6 (OCH ), 57.5 (OCH CH ), 62.3 (OCH ), 111.2 (C6, C11),
2 2 3 2 3 2 2 2
1
14.4 (C7), 119.4 (C9), 120.8 (C2), 121.4, 140.5 (Tz-C), 122.9 (Cα), 123.9 (C4), 128.3 (C8),
29.3 (C10), 131.8 (C3), 139.9 (C5), 143.0 (Cβ), 158.6 (C12), 158.8 (C1), 190.8 (C=O).
1
Anal. Calcd. for C H N O Si: C, 61.07; H, 6.22; N, 10.17. Found: C, 60.98; H, 6.13; N,
2
8
34
4
6
1
0.14.
3
.1.6.18. (E)-1-(3-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2,4-
dimethoxyphenyl)prop-2-en-1-one (9d)
The quantities used were as 6d (1.0 g, 3.1 mmol), AzPSa (0.80 g, 3.1 mmol). Yellow solid,
-1
Yield: 1.65 g, 2.8 mmol, 92 %. IR (neat, cm ): 579 (N→Si), 764, 1096 (Si-O), 1655 (C=N),
1
2
925 (C=C-H). H NMR (400 MHz, CDCl , 25 °C): δ 0.42 (m, 2H, -SiCH -), 2.00 (m, 2H, -
3
2
CCH C-), 2.80 (t, J = 5.8 Hz, 6H, -CH N-), 3.75 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.85 (s, 3H,
2
2
2
2
2
5

ACCEPTED MANUSCRIPT
-
OCH ), 3.90 (s, 3H, -OCH ), 4.33 (t, J = 7.5 Hz, 2H, -N CH -), 5.25 (s, 2H, -OCH -), 6.47
3
3
3
2
2
(s, 1H, H11), 6.53 (d, J = 8.6 Hz, 1H, H9), 7.19 (d, J = 8.6 Hz, 1H, H2), 7.35-7.47 (m, 2H,
Tz-H, H8), 7.52 (d, J = 15.8 Hz, 1H, Hα), 7.58 (d, J = 8.6 Hz, 1H, H4), 7.61-7.64 (m, 1H,
1
3
H3), 7.68 (s, 1H, H6), 8.05 (d, J = 15.8 Hz, 1H, Hβ). C NMR (101 MHz, CDCl , 25 °C): δ
3
1
5
3.2 (SiCH ), 26.3 (CCH C), 51.0 (CH CH N), 53.4 (N CH ), 55.5 (OCH ), 55.6 (OCH ),
2 2 2 2 3 2 3 3
7.5 (OCH CH ), 62.3 (OCH ), 98.5 (C11), 100.0 (C9), 105.4 (C7), 114.3 (C6, C11), 119.2
2
2
2
(C2), 120.4, 140.6 (Tz-C), 121.3 (Cα), 122.9 (C4), 129.6 (C8), 131.0 (C3), 140.3 (C5), 143.1
(
Cβ), 158.5 (C12), 160.5 (C10), 163.1 (C1), 190.8 (C=O). Anal. Calcd. for C H N O Si: C,
29
36
4
7
5
9.98; H, 6.25; N, 9.65. Found: C, 59.83; H, 6.05; N, 9.63.
3
.1.6.19. (E)-1-(3-((1-(3-(silatranyl)propyl)-1H-1,2,3-triazol-4-ylmethoxyphenyl-3-(2,3,4-
trimethoxyphenyl)prop-2-en-1-one (9e)
The quantities used were as 6e (1.0 g, 2.8 mmol), AzPSa (0.72 g, 2.8 mmol). Yellow solid,
-1
Yield: 1.54 g, 2.5 mmol, 91 %. IR (neat, cm ): 583 (N→Si), 763, 1092 (Si-O), 1655 (C=N),
1
2
930 (C=C-H). H NMR (400 MHz, CDCl , 25°C): δ 0.43 (m, 2H, -SiCH -), 2.01 (m, 2H, -
3
2
CCH C-), 2.81 (t, J = 5.8 Hz, 6H, -CH N-), 3.75 (t, J = 5.8 Hz, 6H, -OCH CH -), 3.89 (s, 3H,
2
2
2
2
-
OCH ), 3.92 (s, 3H, -OCH ), 3.95 (s, 3H, -OCH ), 4.33 (t, J = 7.5 Hz, 2H, -N CH -), 5.26 (s,
3 3 3 3 2
2
7
7
H, -OCH -), 6.74 (d, J = 8.8 Hz, 1H, H9), 7.21 (d, J = 8.8 Hz, 1H, H8), 7.36 (s, 1H, Tz-H),
2
.42 (d, J = 7.0 Hz, 1H, H2), 7.54 (d, J = 15.8 Hz, 1H, Hα), 7.62 (d, J = 7.7 Hz, 1H, H4),
13
.65 (m, 1H, H3), 7.69 (s, 1H, H6), 8.01 (d, J = 15.8 Hz, 1H, Hβ). C NMR (101 MHz,
CDCl , 25 °C): δ 13.2 (SiCH ), 26.3 (CCH C), 51.0 (CH CH N), 53.4 (N CH ), 56.1
3
2
2
2
2
3
2
(
OCH CH ), 60.9 (OCH ), 61.5 (OCH ), 62.3 (OCH ), 107.3 (C9), 107.7 (C7), 114.4 (C6),
2 2 3 3 2
1
19.4 (C8), 121.3, 142.5 (Tz-C), 122.0 (C2), 122.9 (Cα), 123.9 (C4), 129.6 (C3), 140.0 (C5),
40.2 (C11), 143.1 (Cβ), 153.9 (C12), 155.8 (C10), 158.6 (C1), 190.5 (C=O). Anal. Calcd.
1
for C H N O Si: C, 59.00; H, 6.27; N, 9.17. Found: C, 58.87; H, 6.17; N, 9.08.
3
0
38
4
8
2
6