Microwave-Assisted synthesis of novel 1,2,3-triazole derivatives and their antimicrobial activity

Article abstract of DOI:10.1007/s00044-013-0880-1

An environmentally benign and economic synthesis of 1-[7-(1-benzyl-1H-[1,2, 3]triazol-4-ylmethoxy)-2,2-dimethyl-chroman-6-yl]-3-Aryl-2-propen-1-ones and 1-[5-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-dimethyl-chroman-6-yl] -3-Aryl-propen-1-ones is desc

Full text of DOI:10.1007/s00044-013-0880-1

MEDICINAL
CHEMISTRY
RESEARCH
Med Chem Res
DOI 10.1007/s00044-013-0880-1
ORIGINAL RESEARCH
Microwave-assisted synthesis of novel 1,2,3-triazole derivatives
and their antimicrobial activity
•
•
•
D. Ashok D. Mohan Gandhi G. Srinivas
A. Vikas Kumar
Received: 26 August 2013 / Accepted: 13 November 2013
Ó Springer Science+Business Media New York 2013
Abstract An environmentally benign and economic syn-
thesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-
2,2-dimethyl-chroman-6-yl]-3-aryl-2-propen-1-ones and
1-[5-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-dimethyl-
chroman-6-yl]-3-aryl-propen-1-ones is described. The
procedure takes place by the 1,3-dipolar cycloaddition
(‘‘click-reaction’’) between azides and alkynes catalysed by
copper (I) salts. The simplicity of this reaction and the ease of
formation and purification of the resulting products have
opened new opportunities in generating vast arrays of com-
pounds with biological potential. The structures of the syn-
thesized compounds have been established on the basis of
physical and spectral data. All the synthesized compounds
were tested in vitro for their antibacterial and antifungal
activities. Compounds 8a (R1=H, R2=H, R3=H), 8b (R1=H,
R2=CH3, R3=H), 8d (R1=OCH3, R2=OCH3, R3=H), 8e
(R1=OCH3, R2=OCH3, R3=OCH3), 13a (R1=H, R2=H,
R3=H), 13d (R1=OCH3, R2=OCH3, R3=H) and 13e
(R1=OCH3, R2=OCH3, R3=OCH3) showed significant anti-
microbial properties.
Introduction
1,2,3-Triazoles and its derivatives have emerged rapidly
with the advance of modern heterocyclic chemistry,
promising a variety of medicinal applications such as
antimicrobial (Demaray et al., 2008) anti-HIV (Lazrek
et al., 2001) anticancer (Chen et al., 2011) and antioxidant
(Khan et al., 2010) activities.
Chalcones are known to exhibit various biological
activities (Alvarez et al., 1994), such as antioxidant
(Sathyanarayana et al., 2004), anti-inflammatory (Muk-
herjee et al., 2001), antimalarial (Hsieh et al., 2000), an-
tileishmanial (Ram et al., 2000) and anticancer (Zhai et al.,
1999) activities. Furthermore, they have considerable bio-
logical importance, especially as pesticides (Anto et al.,
1995). It is known that numbers of chroman derivatives are
used as antioxidant for fats and oils (Bergmann and Ger-
icke, 1990; Burrell et al., 1990; Gericke et al., 1991).
Among naturally occurring chromans, vitamin E is very
effective that suppress cellular membranes phospholipids
degradation (Ray et al., 1976) and also exhibits antioxi-
dant, anticancer and cardio protective activities.
Keywords Microwave irradiation ꢀ Click chemistry ꢀ
1,2,3-Triazoles ꢀ Antimicrobial activity
During the past decades, the environment consciousness
has compelled the chemist to make a new twist on old
theme. In this endeavour, Microwave-assisted reactions
have made a landmark and significant contributions to
preserve the green environment by reducing the waste
effluent, remarkable rate enhancement, high yields, greater
selectivity and ease of manipulation.
Electronic supplementary material The online version of this
article (doi:10.1007/s00044-013-0880-1) contains supplementary
material, which is available to authorized users.
Inspired with the biological profile of 1,2,3 triazoles,
chalcones and chroman nuclei, their increasing importance
in pharmaceutical and biological fields, and in connection
with our (Ashok and Shravani, 2008; Ashok et al., 2012)
search on the design and synthesis of pharmacologically
important new heterocycles linked to chroman, it was
D. Ashok (&) ꢀ D. Mohan Gandhi ꢀ G. Srinivas ꢀ
A. Vikas Kumar
Department of Chemistry, Osmania University,
Hyderabad 500 007, India
e-mail: ashokdou@gmail.com
123

Med Chem Res
thought worthwhile to synthesize the titled compounds
with a view to obtain certain chemical entities with active
pharmacophores in a single molecular framework.
(Scheme 2), compound 6, prepared by propargylation of
compound 1, followed by click reaction using CuI in DMF
under MWI gave compound 7. Compound 7 on conden-
sation with aryl aldehydes in alcoholic KOH under MWI
gave compounds 8a–j in excellent yields than route-1
shown in Scheme 2. Compounds, 13a–j were also syn-
thesized by the same procedure as compounds 8a–j shown
in Scheme 3. By comparing the above routes, the target
compounds were synthesized in excellent yields in route-2
(Table 3) to give overall yields of 90–95 % in short reac-
tion time. Whereas in route 1, the overall yields are
50–60 % only and took longer time to complete the reac-
tion. Initially, we have investigated the yields of the click
reaction using CuSO4ꢀ5H2O/sodium ascorbate and CuI in
different solvents like t-BuOH: H2O (2:1), THF and DMF
under both conventional and MWI. In the above investi-
gation, we produced higher yields using CuI in DMF under
MWI (Tables 1, 2, 3).
Microwave-assisted organic synthesis is suited to the
increased demand in industry because of short reaction
times and expanded reaction range, In particular, there is a
requirement in the pharmaceutical industry for a higher
number of novel chemical entities to be produced.
Results and discussion
Chemistry
Herein, we wish to report an efficient, practical and high
yielding method for the synthesis of compounds 8a–j and
13a–j. The starting materials 1-(7-hydroxy-2,2-dimethyl-
chroman-6-yl)-ethanone (1) and 1-(5-hydroxy-2,2-dime-
thyl-chroman-6-yl)-ethanone (2) were prepared from the
mixture of resacetophenone and isoprene using Amberlyst-
15 catalyst in THF and heptanes (Kalena et al., 1997)
shown in Scheme 1. The synthesis of titled compounds 8a–
j and 13a–j was accomplished by two synthetic strategies
and is shown in Schemes 2 and 3. In route-1 (Scheme 2),
the chalcones 4a–j were synthesized from the mixture of
compound 1 and aryl aldehydes in alcoholic KOH under
microwave irradiation (MWI), followed by propargylation
of chalcones 4a–j in dry acetone/K2CO3 gave compounds
5a–j. These compounds upon click reaction using CuI in
DMF under MWI gave compounds 8a–j. In route-2
Structures of synthesized compounds (5, 6, 8a–j, 11, 12,
1
and 13a–j) were characterized by IR, H NMR, 13C NMR
1
and mass spectral analysis. The H NMR spectrum of the
representative compound 8a (dissolved in CDCl3) showed
a singlet for Ar–H5 proton at d 8.29, another singlet for Ar–
H8 proton at d 6.51. Two singlets for O–CH2 and N–CH2
protons appeared at d 5.41 and 5.21 respectively. In the 13
C
NMR spectrum, the signal of C=O carbon appeared at
190.9 ppm, those of O–CH2 and N–CH2 C-atoms appeared
at 63.0 ppm and 54.0 ppm respectively. From, DEPT 135
O-methylene and N-methylene carbons were confirmed by
the signals at 63.0 and 54.0 respectively and two methylene
Scheme 1 Synthesis of 1-
(7-hydroxy-2,2-dimethyl-
chroman-6-yl)-ethanone (1)
and 1-(5-hydroxy-2,2-dimethyl-
chroman-6-yl)-ethanone(2)
HO
OH
O
O
OH
O
Amberlyst-15
O
OH
O
THF, Heptane
Reflux. 24 h
1
2
Scheme 2 Synthesis of 1-[7-(1-
Benzyl-1H-[1,2,3]triazol-4-
ylmethoxy-2,2-dimethyl-
chroman-6-yl]-3-aryl-
propenone (Route-1 and Route-
2)
R1
R1
O
O
O
R2
R3
(c)
O
OH
O
R
2 (b)
Route-1
R3
(a)
5(a-j)
4(a-j)
N
N
4'
1
O
8
5
N
8a
4a
O
7
O
OH
O
R1
R2
2
5'
3
6
4
O
1
R3
8(a-j)
(b)
N
N
O
(a)
Route-2
N
O
O
O
O
(c)
7
6
O
123

Med Chem Res
Scheme 3 Synthesis of 1-[5-(1-
Benzyl-1H-[1,2,3]triazol-4-
ylmethoxy-2,2-dimethyl-
chroman-6-yl]-3-aryl-
propenone (Route-1 and
Route-2). Reagents and
conditions: (a) Ar–CHO 3(a–j),
KOH/EtOH, MWI
R1
R1
(c)
O
O
R2
R3
(b)
O
OH
O
R2
R3
Route-1
(a)
O
10(a-j)
3
2
9(a-j)
4
N
N
4a
N
4'
O
O
O
1
R1
R2
O
OH
O
5
8a
8
5'
(b) propargylbromide, dry
acetone, K2CO3, reflux.
(c) Benzylazide,
6
7
R3
13(a-j)
2
(i) CuSO4ꢀ5H2O,
Sodiumascorbate, H2O/t-BuOH
(2:1), (or) (ii) CuI, DMF or
THF, NEt3 RT or MWI
(b)
Route-2
N
N
N
O
O
O
O
O
O
(a)
(c)
12
11
Table 1 Screening of catalyst and solvent
Entry
Catalyst
Solvent system
Conventional method
MWI
Time (h)
Yield (%)a
Time (h)
Yield (%)a
1
2
3
4
5
6
CuSO4ꢀ5H2O
CuSO4ꢀ5H2O
CuSO4ꢀ5H2O
Cul
t-BuOH/H2O (3:1)
26
26
24
26
26
24
52–54
56–58
62–64
61–64
65–68
72–75
12–15
12–15
8–10
66–68
68–70
75–78
70–73
74–78
88–90
THF
DMF
t-BuOH/H2O (3:1)
12–15
12–15
8–10
Cul
THF
Cul
DMF
MWI microwave irradiation
a
Isolated yields
Table 2 Comparisons of conventional and microwave irradiation methods
Compound
CuSO4ꢀ5H2O
Conventional method
CuI
Conventional method
Microwave method
Microwave method
Time (h)
Yield (%)a
Time (h)
Yield (%)a
Time (h)
Yield (%)a
Time(h)
Yield (%)a
5a
5b
6
24
24
18
24
24
18
62–64
60–62
68–70
60–62
62–64
68–70
9
8
6
9
8
6
75–78
72–74
75–77
75–78
70–72
77–79
24
24
18
24
24
18
72–75
70–72
72–75
72–75
70–72
72–75
10
10
8
88–90
86–88
90–92
86–88
84–86
90–92
9a
9b
11
10
10
8
a
Isolated yields
carbons C3 and C4 were also confirmed by the signals at
32.6 and 21.5 respectively. The GC–MS spectrum exhib-
ited the [M?H]? peak at m/z 480. Thus, on the basis of
above studies 8a has been assigned structure 1-[7-(1-Ben-
zyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-dimethyl-chroman-
6-yl]-3-phenyl-propenone.
Microbiology
Antibacterial activity
All the synthesised compounds were screened in vitro for
their antibacterial activity against two gram positive
123

Med Chem Res
Table 3 Comparison of yields
of 8a–j and 13a–j of route-1 and
route-2
Compound
R1
R2
R3
Route-1 yield (%)a
Route-2 yield (%)a
8a
H
H
H
58
60
55
50
56
60
60
55
65
50
60
58
60
55
58
65
58
56
64
30
94
93
92
90
92
95
94
92
94
86
94
93
94
90
94
93
94
92
93
88
8b
H
CH3
H
8c
H
OCH3
OCH3
OCH3
N(CH3)2
Cl
H
8d
OCH3
OCH3
H
H
8e
OCH3
H
8f
8g
H
H
8h
Cl
Cl
H
8i
H
CH(CH3)2
H
H
8j
NO2
H
H
13a
13b
13c
13d
13e
13f
13g
13h
13i
13j
H
H
H
CH3
H
H
OCH3
OCH3
OCH3
N(CH3)2
Cl
H
OCH3
OCH3
H
H
OCH3
H
H
H
Cl
Cl
H
H
CH(CH3)2
H
H
NO2
H
a
Isolated yields
bacteria Staphylococcus aureus (ATCC-9144), Bacillus
cereus (ATCC-11778) and two gram negative bacteria
Escherichia coli (ATCC-8739), Proteus vulgaris (ATCC-
29213) by the cup-plate agar diffusion method (Revol-
Junelles et al., 1996) at different concentrations (50, 100,
150 and 200 lg/mL). Nutrient agar medium was used for
the antibacterial screening. The Zone of inhibition (in mm)
was compared with standard drug Streptomycin sulphate.
The results are tabulated in Tables 4 and 5.
(15 mm) against S. aureus. Compound 8e (13 mm) showed
maximum potency compare with standard (16 mm) against
B. cereus. Compounds 8a (14.5 mm), 8d (16 mm) and 8e
(16 mm) showed high potency compare with standard
(17 mm) against E. coli. Compounds 8a (13.5 mm) and 8d
(14 mm) exhibited maximum inhibition compare with
standard (16 mm) against P. vulgaris.
Antifungal activity
The investigation of antibacterial screening revealed
that compounds 8a and 13a exhibited maximum zone of
inhibition, indicates that compounds without substitutions
on phenyl ring (benzaldehyde) showed prominent potency
against all bacteria. compounds 8b–e, 8h, 8i, 13b–e, 13h,
and 13i showed moderate zone of inhibition, indicate that
compounds with substitutions at R1 and R2 positions on
phenyl ring with electron donating groups enhances the
antibacterial activity. Compounds with substitution at R1
position with OCH3 and Cl groups showed maximum zone
of inhibition and compounds with substitution at R2 posi-
tion with CH3, OCH3 and Cl groups showed maximum
zone of inhibition. Compounds 8f, 8g, 8i, 13f, 13g, and 13i
showed poor zone of inhibition against all bacterial strains,
indicate that compounds with substitution at R2 position
with N(CH3)2 and CH(CH3)2 groups diminishes the anti-
bacterial potency.
All the synthesised compounds were screened in vitro for
their antifungal activity against Aspergillus Niger (ATCC-
9029), Candida albicans (ATCC-2091) and Aspergillus
foetidus (NCIM-505). Sabouraud’s agar medium was used
for the antifungal screening. Zone of inhibition (in mm)
was compared with standard drug Nystatin. The results are
tabulated in Table 6.
Antifungal activity studies revealed that the compounds
8a, 8d and 8e showed maximum zone of inhibition, com-
pounds 8b, 8f, 8g, 13a, 13d, 13e and 13g showed moderate
zone of inhibition and compounds 8c, 8h, 8i, 8j, 13b, 13c,
13f, 13h, 13i and 13j showed poor antifungal potency. This
study indicates that compounds without substitution on
phenyl ring showed maximum potency and compounds
with substitutions with Cl, OCH3 and CH3 groups showed
moderate zone of inhibition.
Compounds 8a (14 mm), 8d (14 mm), 8e (13.5 mm)
13a (13 mm) and 13e (13 mm) showed maximum zone of
inhibition compare with standard drug streptomycin
Compounds 8a, 8d, 8e, 13d and 13e exhibited maximum
zone of inhibition against A. Niger. Compounds 8a, 8e, 8f
and 13g showed maximum zone of inhibition against
123

Med Chem Res
Table 4 Antibacterial activity of compounds 8a–j and 13a–j against two gram positive bacteria
Compound
Zone of inhibition at different concentrations after 24 h (mm)
S. aureus (ATCC-9144)
B. cereus (ATCC-11778)
50 (lg/mL)
100 (lg/mL)
150 (lg/mL)
200 (lg/mL)
50 (lg/mL)
100 (lg/mL)
150 (lg/mL)
200 (lg/mL)
8a
14.0
13.0
11.0
12.5
11.5
12.0
11.0
13.5
14.0
10.0
12.5
11.0
10.0
13.0
13.0
9.5
17.5
16.0
13.5
15.0
14.0
15.5
13.0
17.0
18.0
12.0
14.0
13.5
12.5
16.0
16.5
12.0
14.0
12.0
13.0
15.0
19.0
19.0
18.0
15.0
17.5
15.0
17.0
14.5
18.0
19.0
13.0
15.5
14.5
14.0
17.0
16.5
14.0
16.0
13.5
14.0
17.5
22.0
20.5
19.5
16.0
19.0
17.0
18.5
16.0
20.0
21.0
15.0
17.0
16.5
15.5
19.0
19.5
16.0
17.5
15.0
16.5
18.5
25.0
12.5
10.0
9.0
14.0
12.0
10.5
12.0
16.0
13.0
10.0
15.0
13.5
9.0
15.0
13.0
12.0
14.0
18.0
15.0
11.0
17.5
15.5
10.0
13.0
14.0
10.0
14.5
14.0
12.0
13.0
12.5
13.5
11.5
23.0
17.0
13.5
13.0
15.5
20.0
16.0
14.0
19.0
18.0
12.5
14.5
16.0
11.5
16.0
15.5
14.0
14.5
13.0
14.0
13.0
26.0
8b
8c
8d
11.0
13.0
10.5
8.0
8e
8f
8g
8h
13.0
12.0
7.0
8i
8j
13a
13b
13c
13d
13e
13f
13g
13h
13i
13j
Std
9.0
11.5
12.0
8.5
10.5
7.5
11.0
11.0
8.0
13.0
12.5
10.5
11.0
10.5
12.5
10.0
20.0
11.5
9.5
9.5
10.0
11.0
9.0
11.0
12.0
15.0
16.0
Std streptomycin sulphate
C. albicans. Compounds 8a and 8e showed maximum zone
of inhibition against A. foetidus.
addition to the composition of nutrient broth. For anti-
fungal screening, inoculum was prepared by transferring a
loopful of fungal stock culture to 100 mL of conical flask
containing 50 mL of Sabouraud’s broth. The composition
of the broth was Glucose 40 g, Peptone 10 g, distilled
water 1,000 mL. Sabouraud’s agar medium was used for
the antifungal screening, contained 20.0 g of agar in
addition to the composition of Sabouraud’s broth.
Biological assay
Antimicrobial activity
The test solutions of the samples were prepared in
dimethylformamide (DMF). The antibiotics: Streptomycin
sulphate was used as standard for antibacterial screening
and Nystatin was used as a standard for antifungal
screening. The antibacterial standard was dissolved in
sterile-distilled water. The antifungal standard was dis-
solved in buffered 70 % propanol.
For antibacterial screening, the agar medium was ster-
ilized by autoclaving at 120 °C for 15 min. The Petri plates
and pipettes were sterilized by dry heat in a hot-air oven at
150 °C for 1 h. About 20 mL of the molten agar medium
was poured in each of sterilized Petri plates and 0.5 mL of
24 h old broth cultures of bacterial strains were added to
the respective Petri plates. The contents of the Petri plates
were mixed thoroughly by rotary motion. After solidifica-
tion of the medium, four cups (diameter 8 mm) were made
with the help of a sterile borer at equal distances.
The microorganisms employed in this study were two
gram positive bacteria such as S. aureus (ATCC-9144) and
B. cereus (ATCC-11778) and two gram negative bacteria
such as Escherichia coli (ATCC-8739) and P. vulgaris
(ATCC-29213) and fungalstrains likeA. niger (ATCC-9029),
Candica albicans (ATCC-2091) and A. foetidus (NCIM-505).
Nutrient broth (pH -7.2) was used for the preparation of
inoculum of bacteria. Nutrient agar medium was used for
the antibacterial screening, contained 20.0 g of agar in
For antifungal activity, the corning sterile Petri plates were
used for investigation. About 20 mL of the molten Sabou-
raud’s agar medium was poured in each of sterilized Petri
plates and 0.5 mL of 24 h old broth cultures of fungal strains
was added to the respective Petri plates. The contents of the
Petri plates were mixed thoroughly by rotary motion. After
123

Med Chem Res
Table 5 Antibacterial activity of compounds 8a–j and 13a–j against two gram negative bacteria
Compound
Zone of inhibition at different concentrations after 24 h (mm)
E. coli (ATCC-8739)
P. vulgaris (ATCC-2913)
50 (lg/mL)
100 (lg/mL)
150 (lg/mL)
200 (lg/mL)
50 (lg/mL)
100 (lg/mL)
150 (lg/mL)
200 (lg/mL)
8a
14.0
13.5
12.0
13.0
12.5
14.0
13.0
16.0
15.0
11.0
10.5
12.0
9.0
16.0
17.0
13.5
15.0
13.0
16.0
14.0
17.5
16.0
12.5
11.5
14.0
11.0
14.5
15.0
12.0
13.0
11.5
13.5
12.0
21.0
19.0
18.0
15.0
16.0
15.5
18.0
17.0
19.0
18.5
15.0
13.0
16.0
12.5
16.5
16.0
14.0
15.0
14.5
14.5
13.5
25.0
22.0
20.5
17.0
18.0
17.0
19.0
18.5
21.5
20.0
17.0
15.5
18.0
14.0
18.0
19.0
16.5
17.0
14.0
16.5
15.0
27.0
13.5
11.5
10.0
12.5
10.0
13.0
12.0
11.5
14.0
8.0
16.0
15.0
13.0
13.0
12.0
15.0
14.5
12.5
16.0
10.0
10.0
12.0
9.0
18.0
17.0
14.0
15.0
13.0
19.0
16.0
15.0
18.0
11.5
12.0
14.0
11.0
14.5
15.0
12.5
13.5
12.0
13.0
12.0
22.0
20.5
20.0
15.5
16.0
15.0
22.0
18.5
17.0
20.0
13.0
14.0
16.0
12.5
16.0
15.0
14.0
15.0
13.5
14.5
14.5
26.0
8b
8c
8d
8e
8f
8g
8h
8i
8j
13a
13b
13c
13d
13e
13f
13g
13h
13i
13j
Std
9.0
10.5
7.5
12.5
12.0
10.0
11.5
10.0
11.5
10.5
17.0
11.0
10.5
8.5
12.5
12.0
10.5
12.0
11.0
12.0
10.5
19.0
10.0
10.0
11.5
9.0
16.0
Std streptomycin sulphate
solidification of the medium, four cups(diameter 8 mm)were
made with the help of a sterile borer at equal distances.
Accurately measured 0.1 mL of four different concen-
trations (50, 100, 150 and 200 lg/mL) of test samples and
0.1 mL of four different concentrations of standard anti-
biotics (50, 100, 150 and 200 lg/mL) were added into the
cups and labelled accordingly. The plates were kept
undisturbed in a cool place for 1 h to allow the solutions to
diffuse into the medium. The nutrient agar plates were then
incubated at 37 °C for 24 h for antibacterial activity. For
antifungal activity, the Sabouraud’s agar plates were then
incubated at 28 °C for 48 h.
precoated 60 F254 silica gel plates. Visualization was done
by exposing to iodine vapour and UV. IR spectra (tmax in
cm-1) were recorded on a Shimadzu FT-IR 8400 S spec-
trometer. The melting points were taken in open capillary
tubes on a Stuart SMP3 melting-point apparatus and are
uncorrected. 1H, 13C NMR spectra were recorded in CDCl3
on a Bruker AVANCE-400 spectrometer using TMS as an
internal standard. (Chemical shift in d, ppm). Mass spectra
were scanned on a shimadzu GCMS-QP 1000 spectrometer
(shimadzu, Tokyo, Japan).
The presence of definite zone of inhibition surrounding
the cups indicated antimicrobial activity. The diameter of
the zone of inhibition was recorded. The experiments were
performed, at least in triplicate.
General procedures
Synthesis of 1-(2,2-dimethyl-7-prop-2-ynyloxy-
chroman-6-yl)-ethanone (6)
Anhydrous K2CO3 (0.94 g, 6.80 mmol, 1.5 eq) was added
Experimental
to
1-(7-hydroxy-2,2-dimethyl-chroman-6-yl)-ethanone
(1 g, 4.50 mmol, 1.0 eq) dissolved in 5 mL dry acetone.
Propargyl bromide 80 % in toluene (0.64 g, 5.40 mmol,
1.2 eq) was added to the mixture. The reaction mixture was
refluxed for about 8 h. After completion of the reaction
(monitored by TLC), the solvent was removed under
Materials
All the reagents and solvents were purchased from com-
mercial sources. Analytical TLC was performed on Merck
123

Med Chem Res
Table 6 Antifungal activity of compounds 8a–j and 13a–j
Compound Zone of inhibition at different concentrations after 24 h (mm)
A. niger (ATCC-9029)
C. albicans (ATCC-2091)
A. foetidus (NCIM-505)
50
100
150
200
50
100
150
200
50
100
150
200
(lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL) (lg/mL)
8a
13.0
12.0
10.0
13.5
14.0
11.5
11.0
10.0
10.5
9.0
15.0
13.0
11.5
15.5
16.0
13.5
12.5
11.0
12.0
11.0
13.5
10.5
11.0
15.5
13.5
12.0
13.0
11.5
12.5
10.5
18.0
16.5
15.0
13.0
17.0
17.5
15.0
14.5
13.0
13.0
12.5
15.5
12.0
13.5
16.5
15.0
13.5
14.0
13.0
13.5
12.0
20.0
19.0
17.0
15.0
19.5
20.0
16.5
16.0
14.0
15.0
14.0
17.0
13.0
15.0
18.5
16.5
15.0
16.0
15.0
16.5
13.5
22.0
12.0
10.5
11.0
11.5
12.5
12.0
10.0
9.0
13.0
12.0
12.5
12.5
13.5
14.0
11.0
10.0
13.0
10.0
12.0
10.5
13.5
12.0
12.0
11.5
13.5
11.0
12.0
11.0
16.0
15.0
13.0
14.0
14.0
16.0
15.5
13.0
12.0
14.5
11.5
13.0
12.0
14.5
14.0
13.5
13.0
14.5
12.5
13.5
12.5
18.0
17.5
15.0
16.0
16.0
18.0
18.0
15.5
14.0
18.0
13.0
14.5
14.0
16.0
15.5
15.0
15.5
16.0
12.5
14.5
14.5
21.0
12.5
10.0
10.5
11.0
12.0
11.5
9.5
14.0
11.5
12.0
12.0
14.0
13.5
10.5
10.0
12.5
9.5
15.0
12.5
14.0
13.5
15.5
15.0
13.0
11.5
14.0
11.0
13.0
12.0
14.0
14.5
12.5
12.5
14.0
12.5
12.0
11.5
19.0
17.0
14.0
15.5
15.0
17.5
17.5
14.5
13.0
16.0
12.5
14.0
13.5
15.5
15.0
14.0
14.0
15.5
13.0
13.5
13.5
20.0
8b
8c
8d
8d
8f
8g
8h
8.5
8i
11.5
8.5
11.0
8.0
8j
13a
13b
13c
13d
13e
13f
13g
13h
13i
13j
Std
12.0
9.5
11.0
9.0
10.5
8.5
11.5
10.5
13.0
12.5
11.0
11.0
13.0
11.5
11.0
10.0
17.0
10.0
12.0
12.0
10.5
11.0
9.5
11.5
11.0
10.5
10.0
12.0
9.5
11.0
10.5
10.0
9.5
11.5
10.0
9.5
10.5
8.0
12.0
9.5
9.0
17.0
15.0
15.0
Std nystatin
reduced pressure and added 30 mL ice cold water, then
extracted with EtOAc and dried over anhydrous Na2SO4.
Crude was purified by column chromatography using
hexane/EtOAc (4:1) as eluent to give compound 6.
azide (1.0 g, 7.5 mmol) and 1-(2,2-dimethyl-7-prop-2-
ynyloxy-chroman-6-yl)-ethanone (1.90 g, 7.50 mmol) 6
dissolved in t-BuOH:H2O (1:1, v/v) (5 mL) and was stirred
under room temperature for 24 h. After completion of the
reaction (monitored by TLC), the resulting mixture was
poured into ice cold water (20 mL), extracted with 30 mL
EtOAc, washed twice with saturated solution of NH4Cl,
twice with brine and dried over Na2SO4. The organic layer
was concentrated in vacuo and the residue was purified by
column chromatography on silica gel eluted with hexane/
EtOAc (2:1) to give compound 7.
Pale yellow solid; m.p.: 60–62 °C; IR (KBr) cm-1: 3,294
(C:C–H), 3,135 (Ar–H), 2,210 (C:C), 1,648 (C=O), 1,226
1
(Ar–C), and 1,118 (Ar–O); H NMR (400 MHz, CDCl3) d
(ppm): 7.63 (s, 1H, Ar–H5), 6.42 (s, 1H, Ar–H8), 4.72 (d, 2H,
O–CH2), 2.73 (t, J = 6.67 Hz, 2H, CH2), 2.60 (s, 3H, CH3),
2.54 (t, 1H, C:C–H), 1.80 (t, J = 6.73 Hz, 2H, CH2), 1.36
(s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d (ppm):
197.7 (C=O), 159.0 (C8a), 157.3 (C7), 132.4 (C5), 120.8 (C6),
114.1 (C4a), 101.3 (C8), 77.9 (C2), 75.9 (C:C–H), 75.7
(C:C–H), 56.2 (O–CH2), 32.6 (C3), 32.0 (CH3), 26.8
(29CH3), 21.4 (C4); MS [M?H]?: 259.
Synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-
ylmethoxy)-2,2-dimethyl-chroman-6-yl)-ethanone (7)
using CuSO4ꢀ5H2O/Sodium ascorbate under microwave
irradiation
Synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-
ylmethoxy)-2,2-dimethyl-chroman-6-yl)-ethanone (7)
using CuSO4ꢀ5H2O/Sodium ascorbate
A mixture of Benzyl azide (1.0 g, 7.5 mmol), 1-(2,2-
dimethyl-7-prop-2-ynyloxy-chroman-6-yl)-ethanone (1.90 g,
7.50 mmol) 6, CuSO4ꢀ5H2O (0.05 g, 0.37 mmol) and sodium
ascarbate (0.22 g, 1.1 mmol) dissolved in t-BuOH:H2O (1:1,
v/v) (5 mL) was subjected to microwave irradiation at 180
watts for 8–010 min. After completion of the reaction
under conventional conditions
CuSO4ꢀ5H2O (0.05 g, 0.37 mmol) and sodium ascorbate
(0.22 g, 1.10 mmol) were added to a mixture of Benzyl
123

Med Chem Res
(monitored by TLC), the resulting mixture was poured into
ice cold water (20 mL), extracted with 30 mL EtOAc,
washed twice with saturated solution of NH4Cl, twice with
brine and dried over Na2SO4. The organic layer was con-
centrated in vacuo and the residue was purified by column
chromatography on silica gel eluted with hexane/EtOAc (2:1)
to give compound 7.
54.2 (N–CH2), 31.9 (C3), 29.7 (CH3), 26.7 (29CH3), 21.4
(C4); MS [M?H]?: 392.
1-(2,2-Dimethyl-7-prop-2-ynyloxy-chroman-6-yl)-3-
tolyl-propenone (5c)
Pale yellow solid; m.p.:159–162 °C; IR (KBr) cm-1: 3,294
(C:C–H), 3,138 (Ar–H), 2,210 (C:C), 1,648 (C=O),
1,615 (C=C), 1,226 (Ar–C), and 1,118 (Ar–O). H NMR
1
Synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-
ylmethoxy)-2,2-dimethyl-chroman-6-yl)-ethanone (7)
using CuI under conventional conditions
(400 MHz, CDCl3): 7.68–7.64 (d, 1H, J = 15.76 Hz, Hb),
7.58–7.55 (m, 2H, Ha, Ar–H5), 7.52–7.51 (m, 2H, Ar–H),
7.18–7.17 (d, 2H, J = 7.68 Hz, Ar–H), 6.45 (s, 1H, Ar–
H8), 4.71 (s, 2H, O–CH2), 2.74 (t, J = 6.67 Hz, 2H, CH2),
2.53 (s, 1H, C:C–H), 2.36 (s, 3H, CH3-), 1.81 (t,
J = 6.73 Hz, 2H, CH2), 1.35 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 191.2 (C=O), 158.6 (C8a),
156.6 (C7), 141.1 (HC=CH), 132.8 (C5), 132.7–127.0 (6C,
Ar–C), 122.0 (HC=CH), 114.1 (C4a), 109.8 (C6), 101.3
(C8), 78.1 (C2), 75.9 (C:C–H), 75.7 (C:C–H), 56.2 (O–
CH2), 32.6 (C3), 32.7 (CH3), 26.9 (29CH3), 21.4 (C4); MS
[M?H]?: 361.
A mixture of Benzyl azide (1.0 g, 7.5 mmol), 1-(2,2-dime-
thyl-7-prop-2-ynyloxy-chroman-6-yl)-ethanone
(1.90 g,
7.50 mmol) 6, triethylamine (0.90 g, 9.00 mmol) and CuI
(0.14 g, 0.75 mmol) in DMF (5 mL) was stirred under room
temperature for 24 h. After completion of the reaction
(monitored by TLC), the resulting mixture was poured into
ice cold water (20 mL), extracted with 30 mL EtOAc,
washed twice with saturated solution of NH4Cl, twice with
brine and dried over Na2SO4. The organic layer was con-
centrated in vacuo and the residue was purified by column
chromatography on silica gel eluted with hexane/EtOAc
(2:1) to give compound 7.
1-(2,2-Dimethyl-5-prop-2-ynyloxy-chroman-6-yl)-3-
tolyl-propenone (10c)
Synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-
ylmethoxy)-2,2-dimethyl-chroman-6-yl)-ethanone (7)
using CuI under microwave irradiation
Pale yellow solid; m.p.: 59–62 °C; IR (KBr) cm-1: 3,294
(C:C–H), 3,138 (Ar–H), 2,210 (C:C), 1,648 (C=O),
1,615 (C=C), 1,226 (Ar–C), and 1,118 (Ar–O); H NMR
1
(400 MHz, CDCl3) d (ppm): 7.63 (d, 1H, J = 15.76 Hz,
Hb), 7.58–7.51 (m, 4H, Ar–H5, Ar–H), 7.18–7.12 (d, 2H,
J = 7.68 Hz, Ar–H), 6.45 (s, 1H, Ar–H8), 4.71 (s, 2H, O–
CH2), 2.74 (t, J = 6.67 Hz, 2H, CH2), 2.53 (s, 1H, C:C–
H), 2.36 (s, 3H, CH3-), 1.81 (t, J = 6.73 Hz, 2H, CH2),
1.35 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d
(ppm): 191.3 (C=O), 159.0 (C8a), 157.3 (C5), 143.6
(HC=CH), 137.3–126.6 (6C, Ar–C), 124.7 (C7), 115.9
(HC=CH), 113.9 (C6), 109.9 (C4a), 107.0 (C8), 77.9 (C2),
75.9 (C:C–H), 75.7 (C:C–H), 63.2 (O–CH2), 32.0 (C3),
26.7 (29CH3), 20.9 (CH3), 17.5 (C4); MS [M?H]?: 361.
A mixture of Benzyl azide (1.0 g, 7.50 mmol), 1-(2,2-dime-
thyl-7-prop-2-ynyloxy-chroman-6-yl)-ethanone
(1.90 g,
7.50 mmol) 6, triethylamine (0.90 g, 9.00 mmol) and CuI
(0.14 g, 0.75 mmol) in DMF (5 mL) was subjected to
microwave irradiation at 180 watts for 8–10 min. After
completion of the reaction (monitored by TLC), the resulting
mixture was poured into ice cold water (20 mL), extracted
with 30 mL EtOAc, washed twice with saturated solution of
NH4Cl, twice with brine and dried over Na2SO4. The organic
layer was concentrated in vacuo and the residue was purified
by column chromatography on silica gel eluted with hexane/
EtOAc (2:1) to give compound 7.
1-(2,2-Dimethyl-5-prop-2-ynyloxy-chroman-6-yl)-
White solid; m.p.: 95–97 °C; IR (KBr) cm-1: 3,138
(Ar–H), 1,648 (C=O), 1,455 (N=N), 1,226 (Ar–C), 1,182
ethanone (11)
1
(C–N) and 1,118 (Ar–O); H NMR (400 MHz, CDCl3) d
Pale yellow solid; m.p.: 60–62 °C; IR (KBr) cm-1: 3,294
(C:C–H), 3,135 (Ar–H), 2,210 (C:C), 1,648 (C=O),
1,226 (Ar–C), and 1,118 (Ar–O); 1H NMR (400 MHz,
CDCl3) d (ppm): 7.63 (d, J = 8.78 Hz, 1H, Ar–H7), 6.42
(d, J = 8.78 Hz, 1H, Ar–H8), 4.73 (d, 2H, O–CH2), 2.73 (t,
J = 6.67 Hz, 2H, CH2), 2.60 (s, 3H, CH3), 2.55 (t, 1H,
C:C–H), 1.80 (t, J = 6.73 Hz, 2H, CH2), 1.36 (s, 6H,
29CH3); 13C NMR (100 MHz, CDCl3) d (ppm): 197.7
(C=O), 159.0 (C8a), 157.3 (C5), 127.6 (C7), 109.3 (C4a),
108.9 (C8), 102.8 (C6), 77.9 (C2), 75.9 (C:C–H), 75.7
(ppm): 7.60 (s, 1H, Ar–H5), 7.53 (s, 1H, triazole-H), 7.42–
7.35 (m, 3H, Ar–H), 7.28 (m, 2H, Ar–H), 6.44 (s, 1H, Ar–
H8), 5.56 (s, 2H, O–CH2), 5.19 (s, 2H, N–CH2), 2.72 (t,
J = 6.67 Hz, 2H, CH2), 2.45 (s, 3H, CH3), 1.79 (t,
J = 6.73 Hz, 2H, CH2), 1.34 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 198.2 (C=O), 159.0 (C8a),
0
157.0 (C7), 144.1 (1,2,3-triazole C4 ), 134.5–124.1 (6C,
0
Ar–C), 128.0 (C5), 123.4 (1,2,3-triazole C5 ), 127.5 (C5),
120.8 (C6), 114.1 (C4a), 101.3 (C8), 75.2, 67.1 (O–CH2),
123

Med Chem Res
(C:C–H), 56.2 (O–CH2), 32.6 (C3), 32.0 (CH3), 26.8
(29CH3), 17.5 (C4); MS [M?H]?: 259.
75.2 (C2), 63.2 (O–CH2), 54.0 (N–CH2), 32.0 (C3), 26.7
(29CH3), 21.8 (C4); MS [M?H]?: 480.
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-ethanone (12)
dimethyl-chroman-6-yl]-3-p-tolyl-propenone (8b)
White solid, m.p.: 95–98 °C; IR (KBr) cm-1: 3,138 (Ar–
H), 1,648 (C=O), 1,455 (N=N), 1,226 (Ar–C), 1,182 (C–N)
Pale yellow solid; m.p.: 155–157 °C; IR (KBr) cm-1
3,133 (Ar–H), 1,649 (C=O), 1,613 (C=C), 1,455 (N=N),
:
1
1
1,231 (Ar–C), 1,141 (C–N) and 1,117 (Ar–O); H NMR
and 1,118 (Ar–O); H NMR (400 MHz, CDCl3) d (ppm):
7.62 (s, 1H, triazole-H), 7.54–7.51 (d, J = 8.78 Hz, 1H,
Ar–H7), 7.45–7.37 (m, 4H, Ar–H), 7.28 (m, 1H, Ar–H),
6.63–6.60 (d, J = 8.78 Hz, 1H, Ar–H), 5.54 (s, 2H, O–
CH2), 5.02 (s, 2H, N–CH2), 2.77 (t, J = 6.67 Hz, 2H,
CH2), 2.54 (s, 3H, CH3), 1.74 (t, J = 6.73 Hz, 2H, CH2),
1.34 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d
(ppm): 198.2 (C=O), 159.0 (C8a), 157.0 (C5), 144.1 (1,2,3-
(400 MHz, CDCl3) d (ppm): 7.60 (m, 3H, J = 17.13 Hz,
Hb, Ar–H), 7.51 (s, 1H, Ar–H5), 7.45–7.30 (m, 5H, Ar–H),
7.18 (m, 2H, Ar–H), 7.0 (d, 2H, Ar–H), 6.51 (s, 1H, Ar–
H8), 5.20 (s, 4H, O–CH2, N–CH2), 2.77 (t, J = 6.67 Hz,
2H, CH2), 2.40 (s, 1H, CH3), 1.83 (t, J = 6.73 Hz, 2H,
CH2), 1.38 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3)
d (ppm): 190.9 (C=O), 160.5 (C8a), 158.9 (C7), 143.6
0
triazole C4 ), 134.5–128.1 (6C, Ar–C), 128.7 (C7), 124.1
0
(HC=CH), 142.4 (1,2,3-triazole C4 ), 137.6–126.9 (12C,
0
(1,2,3-triazole C5 ), 116.4 (C4a), 113.6 (C8), 102.8 (C6),
0
Ar–C), 130.2 (C5), 122.6 (1,2,3-triazole C5 ), 121.7
75.2 (C2), 67.1 (O–CH2), 54.2 (N–CH2), 31.9 (C3), 29.7
(CH3), 26.7 (29CH3), 17.4 (C4); MS [M?H]?: 392.
(HC=CH), 115.9 (C4a), 110.9 (C7), 101.2 (C8), 75.2 (C2),
63.1 (O–CH2), 54.0 (N–CH2), 32.7 (C3), 26.8 (29CH3),
22.4 (C4), 21.5 (CH3); MS [M?H]?: 494.
Synthesis of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-ylmethoxy-
2,2-dimethyl-chroman-6-yl]-3-phenyl-propenone (8)
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(4-methoxy-phenyl-
propenone (8c)
To a mixture of 1-[7-(1-benzyl-1H-[1,2,3]triazol-4-yl-
methoxy-2,2-dimethyl-chroman-6-yl]-ethanone
(0.1 g,
0.25 mmol) 7 and aryl aldehydes (0.25 mmol, 1 eq) 3a–
j in EtOH (5 mL), pellets of KOH (0.01 g, 1.2 eq) was
added and subjected to microwave irradiation at 180 watts
2-4 min. The progress of the reaction was monitored by
TLC. After completion of reaction, it was poured into
crushed ice, carefully neutralized with 3 N HCl and
extracted with EtOAc (15 mL). The organic layer was
concentrated in vacuo and purified by column chromatog-
raphy on silica gel eluted with hexane/EtOAc (3:1) to give
compound 8.
Pale yellow solid; m.p.: 133–135 °C; IR (KBr) cm-1
3,135 (Ar–H), 1,649 (C=O), 1,616 (C=C), 1,459 (N=N),
:
1
1,255 (Ar–C), 1,145 (C–N) and 1,118 (Ar–O); H NMR
(400 MHz, CDCl3) d (ppm): 7.53–7.51 (m, 2H, Hb, Ar–
H5), 7.41–7.31 (m, 4H, Ha, Ar–H), 7.10–7.07 (m, 2H, Ar–
H), 6.91 (d, 2H, Ar–H), 6.46 (s, 1H, Ar–H8), 5.33 (d, 2H,
O–CH2), 4.96 (d, 2H, N–CH2), 3.86 (s, 1H, OCH3), 2.75 (t,
J = 6.67 Hz, 2H, CH2), 1.82 (t, J = 6.73 Hz, 2H, CH2),
1.36 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d
(ppm): 190.3 (C=O), 160.5 (C8a), 159.8 (1C, Ar–C), 158.9
0
(C7), 143.6 (HC=CH), 142.6 (1,2,3-triazole C4 ), 135.1–
0
124.7 (9C, Ar–C), 130.2 (C5), 123.6 (1,2,3-triazole C5 ),
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-phenyl-propenone (8a)
118.7 (HC=CH), 115.9 (C4a), 114.5 (2C, Ar–C), 110.9
(C6), 100.8 (C8), 75.2 (C2), 63.0 (O–CH2), 56.5 (N–CH2),
54.8 (O–CH3), 32.0 (C3), 26.7 (29CH3), 21.8 (C4). MS
[M?H]?: 510.
Pale yellow solid; m.p.: 130–132 °C; IR (KBr) cm-1
3,138 (Ar–H), 1,648 (C=O), 1,615 (C=C), 1,455 (N=N),
1
1,226 (Ar–C), 1,182 (C–N) and 1,118 (Ar–O); H NMR
:
(400 MHz, CDCl3) d (ppm): 8.29 (s, 1H, Ar–H5), 8.16–
8.11 (d, 1H, J = 15.96 Hz, Hb), 7.79–7.51 (m, 7H, Ha, Ar–
H), 7.20–7.12 (m, 3H, Ar–H), 7.11–7.09 (m, 2H, Ar–H),
6.51 (s, 1H, Ar–H8), 5.41 (s, 2H, O–CH2), 5.21 (s, 2H, N–
CH2), 2.76 (t, J = 7.02 Hz, 2H, CH2), 1.83 (t,
J = 7.02 Hz, 2H, CH2), 1.37 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 190.9 (C=O), 160.5 (C8a),
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(3,4-dimethoxy-phenyl)-
propenone (8d)
Pale yellow solid; m.p.: 122–124 °C; IR (KBr) cm-1
3,064 (Ar–H), 1,668 (C=O), 1,606 (C=C), 1,461 (N=N),
1
1,265 (Ar–C), 1,141 (C–N) and 1,119 (Ar–O); H NMR
:
0
158.9 (C7), 143.6 (HC=CH), 142.6 (1,2,3-triazole C4 ),
(400 MHz, CDCl3) d (ppm): 7.61–7.54 (m, 3H, Hb, Ar–H5,
Ar–H), 7.43–7.38 (m, 3H, Ar–H), 7.24–7.23 (m, 4H, Ha,
Ar–H), 7.11–7.01 (m, 3H, Ar–H), 6.88–6.85 (d,
135.1–124.7 (12C, Ar–C), 130.2 (C5), 123.6 (1,2,3-triazole
0
C5 ), 118.7 (HC=CH), 115.9 (C4a), 110.9 (C6), 100.8 (C8),
123

Med Chem Res
J = 8.16 Hz, 1H, Ar–H), 6.47 (s, 1H, Ar–H8), 5.25 (s, 2H,
O–CH2), 5.20 (s, 2H, N–CH2), 3.92 (d, J = 17.37 Hz, 6H,
29CH3), 2.74 (t, J = 6.79 Hz, 2H, CH2), 1.82 (t,
J = 6.79 Hz, 2H, CH2), 1.34 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 190.3 (C=O), 160.5 (C8a),
158.9 (C7), 149.3 (2C, Ar–C), 143.6 (HC=CH), 142.6
112.7 (2C, Ar–C), 110.9 (C6), 100.8 (C8), 75.7 (C2), 63.2
(O–CH2), 56.2 (N–CH2), 40.1 (29N–CH3), 32.0 (C3), 26.7
(29CH3), 21.8 (C4); MS [M?H]?: 523.
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(4-chloro-phenyl)-
propenone (8g)
0
(1,2,3-triazole C4 ), 135.1–124.7 (8C, Ar–C), 130.2 (C5),
0
123.6 (1,2,3-triazole C5 ), 118.7 (HC=CH), 115.9 (C4a),
Pale yellow solid; m.p.: 152–154 °C; IR (KBr) cm-1
3,136 (Ar–H), 1,653 (C=O), 1,569 (C=C), 1,491 (N=N),
:
112.5 (2C, Ar–C), 110.9 (C6), 100.8 (C8), 75.2 (C2), 63.2
(O–CH2), 56.5 (N–CH2), 54.8 (29O–CH3), 32.0 (C3), 26.7
(29CH3), 21.8 (C4); MS [M?H]?: 540.
1
1,281 (Ar–C), 1,142 (C–N) and 1,118 (Ar–O); H NMR
(400 MHz, CDCl3) d (ppm): 7.60–7.54 (m, 3H, Hb, Ar–
H5), 7.39–7.30 (m, 8H, Ha, Ar–H), 7.08–7.06 (dd, 2H, Ar–
H), 6.49 (s, 1H, Ar–H8), 5.32 (s, 2H, O–CH2), 5.19 (s, 2H,
N–CH2), 2.76 (t, J = 7.02 Hz, 2H, CH2), 1.82 (t,
J = 7.02 Hz, 2H, CH2), 1.36 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 190.5 (C=O), 171.1 (C8a),
1-[7-(1-Benzyl-1 H-[1,2,3] triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(3,4,5-trimethoxy-phenyl)-
propenone (8e)
Pale yellow solid; m.p.: 70–72 °C; IR (KBr) cm-1: 3,138
(Ar–H), 1,653 (C=O), 1,615 (C=C), 1,455 (N=N), 1,279
(Ar–C), 1,182 (C–N) and 1,118 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.56 (s, 1H, Ar–H5), 7.51 (s,
1H, Ar–H), 7.46–7.40 (d, J = 15.86 Hz, 1H, Hb), 7.38 (s,
1H, Ar–H), 7.28–7.21 (m, 3H, Ha, Ar–H), 7.03–7.00 (dd,
1H, Ar–H), 6.75 (s, 2H, Ar–H), 6.47 (s, 1H, Ar–H8), 5.26
(s, 2H, O–CH2), 5.19 (s, 2H, N–CH2), 3.88 (s, 3H, 19O–
CH3), 3.85 (s, 6H, 29O–CH3), 2.76 (t, J = 6.78 Hz, 2H,
CH2), 1.82 (t, J = 6.13 Hz, 2H, CH2), 1.36 (s, 6H,
29CH3); 13C NMR (100 MHz, CDCl3) d (ppm): 190.9
(C=O), 171.2 (C8a), 158.9 (C7), 156.9 (2C, Ar–C), 143.6
0
159.1 (C7), 143.6 (HC=CH), 141.1 (1,2,3-triazole C4 ),
135.1–124.7 (12C, Ar–C), 130.2 (C5), 123.6 (1,2,3-triazole
0
C5 ), 118.7 (HC=CH), 115.9 (C4a), 110.9 (C6), 100.8 (C8),
75.2 (C2), 63.0 (O–CH2), 54.1 (N–CH2), 32.0 (C3), 26.8
(29CH3), 21.1 (C4); MS [M?H]?: 514.
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(3,4-dichloro-phenyl)-
propenone (8h)
Pale yellow solid; m.p.: 95–97 °C; IR (KBr) cm-1: 3,139
(Ar–H), 1,660 (C=O), 1,568 (C=C), 1,491 (N=N), 1,287
(Ar–C), 1,157 (C–N) and 1,109 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.61 (s, 1H, Ar–H5),7.55–7.54
(d, J = 15.99 Hz, 2H, Hb, Ar–H), 7.49–7.41 (m, 3H, Ha,
Ar–H), 7.31–7.29 (m, 4H, Ar–H), 7.13–7.11 (d,
J = 6.99 Hz, 2H, Ar–H), 6.49 (s, 1H, Ar–H8), 5.40 (s, 2H,
O–CH2), 5.21 (s, 2H, N–CH2), 2.77 (t, J = 6.99 Hz, 2H,
CH2), 1.84 (t, J = 6.99 Hz, 2H, CH2), 1.38 (s, 6H,
29CH3); 13C NMR (100 MHz, CDCl3) d (ppm): 197.1
(C=O), 171.1 (C8a), 159.2 (C7), 143.5 (HC=CH), 141.0
0
(HC=CH), 142.6 (1,2,3-triazole C4 ), 135.1–125.4 (7C, Ar–
0
C), 130.2 (C5), 123.6 (1,2,3-triazole C5 ), 118.7 (HC=CH),
115.9 (C4a), 110.9 (C6), 104.3 (2C, Ar–C), 100.8 (C8), 75.7
(C2), 63.2 (O–CH2), 60.9 (19O–CH3), 56.2 (N–CH2), 56.0
(29O–CH3), 32.0 (C3), 26.7 (29CH3), 21.8 (C4); MS
[M?H]?:570.
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(4-dimethylamino-phenyl)-
propenone (8f)
0
(1,2,3-triazole C4 ), 135.2–124.7 (12C, Ar–C), 130.8 (C5),
Yellow solid; m.p.: 113–115 °C; IR (KBr) cm-1: 3,137
(Ar–H), 1,647 (C=O), 1,606 (C=C), 1,491 (N=N), 1,275
(Ar–C), 1,140 (C–N) and 1,116 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.64–7.60 (d, J = 15.99 Hz,
1H, Hb), 7.54 (s, 1H, Ar–H5), 7.42–7.40 (m, 3H, Ar–H),
7.34–7.26 (m, 4H, Ha, Ar–H), 7.04–7.02 (d, J = 6.99 Hz,
2H, Ar–H), 6.69–6.67 (d, J = 7.99 Hz, 2H, Ar–H), 6.47 (s,
1H, Ar–H8), 5.22 (s, 4H, O–CH2, N–CH2), 3.03 (s, 6H,
29CH3), 2.77 (t, J = 6.99 Hz, 2H, CH2), 1.83 (t,
J = 6.99 Hz, 2H, CH2), 1.38 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 191.4 (C=O), 159.1 (C8a),
158.2 (C7), 151.9 (1C, Ar–C), 144.0 (HC=CH), 143.8
0
123.6 (1,2,3-triazole C5 ), 118.7 (HC=CH), 115.9 (C4a),
110.9 (C6), 100.8 (C8), 75.3 (C2), 63.2 (O–CH2), 54.1 (N–
CH2), 31.9 (C3), 26.7 (29CH3), 21.1 (C4); MS
[M?H]?:549.
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
dimethyl-chroman-6-yl]-3-(4-isopropyl-phenyl)-
propenone (8i)
Pale yellow solid; m.p.: 115–117 °C; IR (KBr) cm-1
3,135 (Ar–H), 1,665 (C=O), 1,609 (C=C), 1,468 (N=N),
:
1
1,211 (Ar–C), 1,176 (C–N) and 1,121 (Ar–O); H NMR
0
(1,2,3-triazole C4 ), 135.1–125.4 (9C, Ar–C), 130.2 (C5),
0
123.6 (1,2,3-triazole C5 ), 118.7 (HC=CH), 115.9 (C4a),
(400 MHz, CDCl3) d (ppm): 7.59–7.52 (m, 2H, Hb, Ar–
123

Med Chem Res
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
H5), 7.46–7.43 (d, J = 15.86 Hz, 1H, Ha), 7.40–7.36 (m,
4H, Ar–H), 7.26–7.20 (m, 4H, Ar–H), 6.98–6.95 (dd, 2H,
Ar–H), 6.46 (s, 1H, Ar–H8), 5.20 (s, 2H, O–CH2), 5.17 (s,
2H, N–CH2), 2.98–2.89 (m, 1H, C–H), 2.76 (t,
J = 6.67 Hz, 2H, CH2), 1.82 (t, J = 6.67 Hz, 2H, CH2),
1.36 (s, 6H, 29CH3), 1.27 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 190.2 (C=O), 163.2 (C8a),
158.8 (C7), 150.5 (1C, Ar–C), 143.6 (HC=CH), 142.9
dimethyl-chroman-6-yl]-3-p-tolyl-propenone (13b)
Pale yellow solid; m.p.: 98–100 °C; IR (KBr) cm-1: 3,152
(Ar–H), 1,645 (C=O), 1,592 (C=C), 1,495 (N=N), 1,222
(Ar–C), 1,164 (C–N) and 1,118 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.70 (d, J = 15.67 Hz, 1H,
Hb), 7.65–7.45 (m, 5H, Ar–H7, Ha, Ar–H), 7.33–7.32 (m,
3H, Ar–H), 7.20–7.17 (d, J = 8.10 Hz, 2H, Ar–H), 7.09–
7.08 (m, 2H, Ar–H), 6.69–6.66 (d, J = 8.87 Hz, 1H, Ar–
H8), 5.32 (s, 2H, O–CH2), 4.96 (s, 2H, N–CH2), 2.81 (t,
J = 6.06 Hz, 2H, CH2), 2.3 (s, 1H, CH3), 1.8 (t,
J = 6.67 Hz, 2H, CH2), 1.33 (s, 6H, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 190.9 (C=O), 160.5 (C8a),
0
(1,2,3-triazole C4 ), 135.1–124.7 (11C, Ar–C), 130.2 (C5),
0
123.6 (1,2,3-triazole C5 ), 118.7 (HC=CH), 115.9 (C4a),
110.9 (C6), 100.8 (C8), 75.2 (C2), 63.2 (O–CH2), 53.9 (N–
CH2), 34.1 (CH–29CH3), 32.0 (C3), 26.8 (29CH3), 23.8
(CH–29CH3), 21.1 (C4); MS [M?H]?: 522.
0
158.9 (C5), 143.6 (1,2,3-triazole C4 ), 142.6 (HC=CH),
1-[7-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy-2,2-
137.3–126.6 (12C, Ar–C), 124.7 (C7), 123.6 (1,2,3-triazole
dimethyl-chroman-6-yl]-3-(3-nitro-phenyl)-propenone (8j)
0
C5 ), 115.9 (HC=CH), 113.9 (C6), 109.9 (C4a), 107.0 (C8),
75.2 (C2), 67.8 (O–CH2), 54.0 (N–CH2), 32.0 (C3), 26.7
(29CH3), 21.3 (CH3), 17.5 (C4); MS [M?H]?: 494.
Pale yellow solid; m.p.: 100–102 °C; IR (KBr) cm-1
3,140 (Ar–H), 1,653 (C=O), 1,615 (C=C), 1,455 (N=N),
:
1
1,279 (Ar–C), 1,182 (C–N) and 1,118 (Ar–O); H NMR
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
dimethyl-chroman-6-yl]-3-(4-methoxy-phenyl)-
propenone (13c)
(400 MHz, CDCl3) d (ppm): 7.80–7.75 (m, 2H, Ar–H),
7.54–7.52 (d, J = 16.30 Hz, 1H, Hb), 7.46 (s, 1H, Ar–H5),
7.43–7.31 (m, 4H, Ha, Ar–H), 7.21–7.15 (m, 2H, Ar–H),
7.11–7.08 (d, 1H, Ar–H), 6.98–9.95 (m, 2H, Ar–H), 6.46
(s, 1H, Ar–H8), 5.20 (s, 2H, O–CH2), 5.17 (s, 2H, N–CH2),
2.76 (t, J = 6.67 Hz, 2H, CH2), 1.82 (t, J = 6.73 Hz, 2H,
CH2), 1.36 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3)
d (ppm): 189.9 (C=O), 163.2 (C8a), 159.4 (C7), 148.6 (1C,
Pale yellow solid; m.p.: 90–92 °C; IR (KBr) cm-1: 3,140
(Ar–H), 1,649 (C=O), 1,605 (C=C), 1,485 (N=N), 1,221
(Ar–C), 1,172 (C–N) and 1,108 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.67 (d, 1H, Ar–H7), 7.55 (dd,
J = 12.16 Hz, 1H, Hb), 7.40 (d, J = 6.74 Hz, Ar–H), 7.29
(m, Ar–H), 7.08 (dd, J = 12.27 Hz, 1H, Ha), 6.7 (d, 1H,
Ar–H8), 5.31 (s, 2H, O–CH2), 5.21 (s, 2H, N–CH2), 2.81 (t,
J = 6.67 Hz, 2H, CH2), 1.76 (t, J = 6.66 Hz, 2H, CH2),
1.33 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d
(ppm): 190.3 (C=O), 160.5 (C8a), 158.9 (C5), 157.2 (1C,
0
Ar–C), 143.6 (HC=CH), 142.9 (1,2,3-triazole C4 ), 139.6–
0
124.7 (11C, Ar–C), 130.2 (C5), 123.6 (1,2,3-triazole C5 ),
118.7 (HC=CH), 115.9 (C4a), 110.9 (C6), 100.8 (C8), 75.2
(C2), 63.0 (O–CH2), 53.9 (N–CH2), 32.0 (C3), 26.8
(29CH3), 21.1 (C4); MS [M?H]?: 525.
0
Ar–C), 143.6 (1,2,3-triazole C4 ), 142.6 (HC=CH), 134.3–
0
126.6 (9C, Ar–C), 124.7 (C7), 123.6 (1,2,3-triazole C5 ),
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
115.9 (HC=CH), 114.8 (2C, Ar–C), 113.9 (C6), 109.9
(C4a), 107.0 (C8), 75.2 (C2), 67.2 (O–CH2), 54.0 (N–CH2),
52.8 (O–CH3), 32.0 (C3), 26.7 (29CH3), 17.5 (C4); MS
[M?H]?: 510.
dimethyl-chroman-6-yl]-3-phenyl-propenone (13a)
White solid; m.p.: 98–100 °C; IR (KBr) cm-1: 3,139 (Ar–
H), 1,661 (C=O), 1,594 (C=C), 1,453 (N=N), 1,226 (Ar–
1
C), 1,165 (C–N) and 1,119 (Ar–O); H NMR (400 MHz,
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
dimethyl-chroman-6-yl]-3-(3,4-dimethoxy-phenyl)-
propenone (13d)
CDCl3) d (ppm): 7.71–7.67 (d, 2H, Hb, Ar–H7,), 7.58–7.53
(m, 4H, Ha, Ar–H), 7.40 (m, 4H, Ar–H), 7.26 (m, 2H, Ar–
H), 7.10–7.07 (d, 2H, Ar–H), 6.68–6.65 (d, J = 9.09 Hz,
1H, Ar–H8), 5.31 (s, 2H, O–CH2), 4.96 (s, 2H, N–CH2),
2.80 (t, J = 7.02 Hz, 2H, CH2), 1.76 (t, J = 7.02 Hz, 2H,
CH2), 1.33 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3)
d (ppm): 190.9 (C=O), 158.9 (C8a), 157.1 (C5), 143.6
White solid; m.p.: 92–95 °C; IR (KBr) cm-1: 3,050 (Ar–
H), 1,658 (C=O), 1,611 (C=C), 1,476 (N=N), 1,227 (Ar–
1
C), 1,180 (C–N) and 1,121 (Ar–O); H NMR (400 MHz,
0
(1,2,3-triazole C4 ), 142.6 (HC=CH), 135.1–126.6 (12C,
CDCl3) d (ppm): 7.66–7.62 (d, J = 16.06 Hz, 1H, Hb),
7.55–7.53 (d, J = 9.03 Hz, 1H, Ar–H7), 7.51–7.26 (m, 3H,
Ha, Ar–H), 7.10–6.86 (m, 5H, Ar–H), 6.84–6.67 (d, 1H,
Ar–H), 6.64–6.63 (d, J = 9.03 Hz, 1H, Ar–H8), 5.34 (s,
2H, O–CH2), 5.02 (s, 2H, N–CH2), 3.88 (s, 6H, 29CH3),
0
Ar–C), 124.7 (C7), 123.6 (1,2,3-triazole C5 ), 115.9
(HC=CH), 113.9 (C6), 109.9 (C4a), 107.0 (C8), 75.2 (C2),
67.7 (O–CH2), 54.0 (N–CH2), 32.0 (C3), 26.7 (29CH3),
17.5 (C4); MS [M?H]?: 480.
123

Med Chem Res
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
2.80 (t, J = 7.02 Hz, 2H, CH2), 1.76 (t, J = 7.02 Hz, 2H,
CH2), 1.30 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3)
d (ppm): 190.3 (C=O), 160.5 (C8a), 158.9 (C5), 150.1 (2C,
dimethyl-chroman-6-yl]-3-(4-chloro-phenyl)-
propenone (13g)
0
Ar–C), 143.6 (1,2,3-triazole C4 ), 142.6 (HC=CH), 134.3–
Pale yellow solid; m.p.: 150–152 °C; IR (KBr) cm-1
3,150 (Ar–H), 1,648 (C=O), 1,591 (C=C), 1,486 (N=N),
:
0
125.2 (8C, Ar–C), 124.7 (C7), 123.6 (1,2,3-triazole C5 ),
115.9 (HC=CH), 113.9 (C6), 111.8 (2C, Ar–C), 109.9
(C4a), 107.0 (C8), 75.2 (C2), 67.7 (O–CH2), 54.0 (N–CH2),
52.8 (29O–CH3), 32.0 (C3), 26.7 (29CH3), 17.5 (C4); MS
[M?H]?: 540.
1
1,216 (Ar–C), 1,165 (C–N) and 1,120 (Ar–O); H NMR
(400 MHz, CDCl3) d (ppm): 7.64–7.60 (d, J = 16.06 Hz,
1H, Hb), 7.56–7.46 (m, 4H, Ha, Ar–H7, Ar–H),7.35–
7.31(m, 5H, Ar–H), 7.24 (d, J = 9.78 Hz, 1H, Ar–H),
7.14–7.11 (m, 2H, Ar–H), 6.67–6.65 (d, J = 8.53 Hz, 1H,
Ar–H8), 5.37 (s, 2H, O–CH2), 4.95 (s, 2H, N–CH2), 2.79 (t,
J = 7.02 Hz, 2H, CH2), 1.77 (t, J = 7.02 Hz, 2H, CH2),
1.33 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d
(ppm): 190.5 (C=O), 171.1 (C8a), 159.0 (C5), 143.6 (1,2,3-
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
dimethyl-chroman-6-yl]-3–(3,4,5-trimethoxy-phenyl)-
propenone (13e)
Pale yellow solid; m.p.: 93–95 °C; IR (KBr) cm-1: 3,137
(Ar–H), 1,659 (C=O), 1,592 (C=C), 1,503 (N=N), 1,235
(Ar–C), 1,162 (C–N) and 1,124 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.61–7.57 (d, J = 16.06 Hz,
1H, Hb), 7.54–7.53 (d, J = 8.78 Hz, 1H, Ar–H7), 7.45–
7.31 (m, 7H, Ha, Ar–H), 6.78 (s, 2H, Ar–H), 6.67–6.65 (d,
J = 8.78 Hz, 1H, Ar–H8), 5.34 (s, 2H, O–CH2), 4.97 (s,
2H, N–CH2), 3.91 (s, 9H, 39CH3), 2.80 (t, J = 7.27 Hz,
2H, CH2), 1.83 (t, J = 7.02 Hz, 2H, CH2), 1.32 (s, 6H,
29CH3); 13C NMR (100 MHz, CDCl3) d (ppm): 190.9
(C=O), 158.8 (C8a), 156.9 (C5), 153.5 (2C, Ar–C), 143.6
0
triazole C4 ), 141.1 (HC=CH), 134.3–126.6 (12C, Ar–C),
0
124.7 (C7), 123.6 (1,2,3-triazole C5 ), 115.9 (HC=CH),
114.0 (C6), 109.9 (C4a), 107.0 (C8), 75.2 (C2), 67.8 (O–
CH2), 54.0 (N–CH2), 31.9 (C3), 26.7 (29CH3), 17.5 (C4);
MS [M?H]?: 514.
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
dimethyl-chroman-6-yl]-3-(3,4-dichloro-phenyl)-
propenone (13h)
Pale yellow solid; m.p.: 97–99 °C; IR (KBr) cm-1: 3,140
(Ar–H), 1,644 (C=O), 1,593 (C=C), 1,467 (N=N), 1,220
(Ar–C), 1,169 (C–N) and 1,118 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.84–7.82 (d, J = 8.78 Hz,
1H, Ar–H7), 7.68–7.63 (d, J = 15.05 Hz, 1H, Hb), 7.61–
7.50(m, 2H, Ar–H), 7.42–7.33 (m, 7H, Ha, Ar–H), 7.15–
7.13 (m, 2H, Ar–H), 6.68–6.65 (d, J = 8.78 Hz, 1H, Ar–
H8), 5.41 (s, 2H, O–CH2), 4.96 (s, 2H, N–CH2), 2.80 (t,
J = 7.02 Hz, 2H, CH2), 1.77 (t, J = 7.02 Hz, 2H, CH2),
1.33 (s, 6H, 29CH3); 13C NMR (100 MHz, CDCl3) d
(ppm): 197.1 (C=O), 171.1 (C8a), 159.2 (C5), 143.5 (1,2,3-
0
(1,2,3-triazole C4 ), 142.6 (HC=CH), 134.3–125.9 (8C, Ar–
0
C), 124.7 (C7), 123.6 (1,2,3-triazole C5 ), 115.9 (HC=CH),
113.9 (C6), 109.9 (C4a), 107.0 (C8), 105.6 (2C, Ar–C), 75.1
(C2), 67.7 (O–CH2), 60.8 (19O–CH3), 56.2 (29O–CH3),
54.0 (N–CH2), 32.0 (C3), 26.7 (29CH3), 17.5 (C4); MS
[M?H]?: 570.
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
dimethyl-chroman-6-yl]-3-(4-dimethylamino-phenyl)-
propenone (13f)
0
triazole C4 ), 139.7 (HC=CH), 135.2–127.7 (12C, Ar–C),
Yellow solid; m.p.: 95–97 °C; IR (KBr) cm-1: 3,136 (Ar–
H), 1,646 (C=O), 1,594 (C=C), 1,476 (N=N), 1,227 (Ar–
0
124.7 (C7), 123.6 (1,2,3-triazole C5 ), 115.9 (HC=CH),
113.9 (C6), 109.9 (C4a), 107.0 (C8), 75.2 (C2), 67.8 (O–
CH2), 54.1 (N–CH2), 34.8 (C3), 26.7 (29CH3), 17.5 (C4);
MS [M?H]?: 549.
1
C), 1,165 (C–N) and 1,118 (Ar–O); H NMR (400 MHz,
CDCl3) d (ppm): 7.69–7.65 (d, J = 15.81 Hz, 1H, Hb),
7.51–7.46 (m, 3H, Ar–H7, Ar–H), 7.34–7.28 (m, 5H, Ar–
H), 7.08–7.06 (m, 2H, Ar–H), 6.68–6.63 (m, 3H, Ar–H8,
Ar–H), 5.31 (s, 2H, O–CH2), 4.98 (s, 2H, N–CH2), 3.10 (s,
6H, 29CH3), 2.81 (t, J = 7.27 Hz, 2H, CH2), 1.76 (t,
J = 7.02 Hz, 2H, CH2), 1.33 (s, 29CH3); 13C NMR
(100 MHz, CDCl3) d (ppm): 191.4 (C=O), 158.2 (C8a),
1-[5-(1-Benzyl-1H-[1,2,3]triazol-4-ylmethoxy)-2,2-
dimethyl-chroman-6-yl]-3-(4-isopropyl-phenyl)-
propenone (13i)
Pale yellow solid; m.p.: 95–97 °C; IR (KBr) cm-1: 3,146
(Ar–H), 1,667 (C=O), 1,611 (C=C), 1,475 (N=N), 1,229
(Ar–C), 1,186 (C–N) and 1,098 (Ar–O); 1H NMR
(400 MHz, CDCl3) d (ppm): 7.70–7.66 (d, J = 16.06 Hz,
1H, Hb), 7.54–7.46 (m, 5H, Ar–H7, Ar–H), 7.35–7.29 (m,
5H, Ha, Ar–H), 7.08–7.06 (m, 2H, Ar–H), 6.67–6.64 (d,
J = 8.78 Hz, 1H, Ar–H8), 5.30 (s, 2H, O–CH2), 4.97 (s,
0
156.5 (C5), 151.9 (1C, Ar–C), 144.0 (1,2,3-triazole C4 ),
143.8 (HC=CH), 134.5–125.4 (9C, Ar–C), 124.7 (C7),
0
123.6 (1,2,3-triazole C5 ), 115.7 (HC=CH), 113.9 (C6),
111.3 (2C, Ar–C), 109.9 (C4a), 107.0 (C8), 74.9 (C2), 67.5
(O–CH2), 53.9 (N–CH2), 40.1 (29N–CH3), 32.0 (C3), 26.7
(29CH3), 17.5 (C4); MS [M?H]?: 523.
123

Med Chem Res
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Acknowledgments The authors are thankful to The Head, Depart-
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Laboratory facilities and one of the authors D. Mohan Gandhi
thankful to UGC, New Delhi, India for financial support in the form
of UGC-SRF. We also thankful to The Director, CFRD, Osmania
University, Hyderabad for providing spectral analysis facilities.
123

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123