An efficient, multicomponent synthesis of aminoalkylnaphthols via Betti reaction using ZSM-5 as a recoverable and reusable catalyst

Article abstract of DOI:10.1002/aoc.6316

The design and application of environmentally friendly catalysts to reduce the number of toxic wastes are critical for improving the chemical synthetic protocols. A simple, mild, efficient, and eco-friendly method was developed for the synthesis of a seri

Full text of DOI:10.1002/aoc.6316

Received: 26 February 2021
DOI: 10.1002/aoc.6316
Revised: 10 May 2021
Accepted: 10 May 2021
F U L L P A P E R
An efficient, multicomponent synthesis of
aminoalkylnaphthols via Betti reaction using ZSM-5 as a
recoverable and reusable catalyst
Rangappa S. Keri1
| Mahadeo Patil1
| Srinivasa Budagumpi1
|
Balappa S. Sasidhar2,3
1Centre for Nano and Material Sciences,
Jain University, Jain Global Campus,
Bangalore, India
2Academy of Scientific and Innovative
Research (AcSIR), New Delhi, India
3Organic Chemistry Section, Chemical
Sciences and Technology Division,
Council of Scientific and Industrial
Research (CSIR), National Institute for
Interdisciplinary Science and Technology
(NIIST), Thiruvananthapuram, India
The design and application of environmentally friendly catalysts to reduce the
number of toxic wastes are critical for improving the chemical synthetic
protocols. A simple, mild, efficient, and eco-friendly method was developed
for the synthesis of a series of Betti bases, 1-(α-aminoalkyl)naphthols, via a
one-pot, multi-component reaction from aldehydes, β-naphthol and secondary
amines in the presence of H-ZSM-5 as a catalyst at room temperature. The key
advantages of the new protocol are environmentally friendly as it offers some
interesting promising reaction prerequisites such as mild condition, safe,
minimal waste, low cost, short reaction time and atom efficiency, easy workup,
high to excellent yields, and possessing excellent functional group tolerance to
synthesize structurally diverse derivatives. The catalyst is readily recovered by
simple decantation and recycled several times with no significant loss in the
catalytic activity.
Correspondence
Rangappa S. Keri, Organic and Medicinal
Chemistry Laboratory, Centre for Nano
and Material Sciences, Jain University,
Jain Global Campus, Jakkasandra Post,
Kanakapura Road, Ramanagara District,
Bangalore, Karnataka 562112, India.
Email: keriphd@gmail.com;
K E Y W O R D S
sk.rangappa@jainuniversity.ac.in
aminoalkylnaphthols, Betti reaction, catalyst, X-ray diffraction, ZSM-5
Funding information
Nanomission, Grant/Award Number:
SR/NM/NS-20/2014; Jain University
1 | INTRODUCTION
MCRs are rather environmentally benign and atom eco-
nomic, as they require short reaction time and avoid
Multicomponent reactions (MCRs) are an important class
of synthetic protocols in organic and medicinal chemistry
with green chemistry criteria such as high degree of atom
economy, waste prevention, no usage of hazardous com-
pounds, energy efficiency, and applications in combinato-
rial chemistry.[1] These reactions are single step one-pot
transformations proceeding through more than two sub-
sequent reactions in which the product of the first is a
substrate for the second.[2,3] Also, these reactions consti-
tute an especially attractive synthetic strategy as they pro-
vide easy and rapid access to large libraries of organic
compounds with diverse substitution patterns. Besides,
costly purification processes as well as protection–
deprotection steps.[4] During the past few decades, many
one-pot MCRs have been reported for the construction of
new carbon–carbon, carbon–heteroatom, and hetero
atom–hetero atom bonds.[5–7] One of the important reac-
tions in the field of MCRs is the synthesis of Betti bases,
which is found to be much crucial due to its unique and
wide spread applications. The first ever work on these
derivatives was reported in the beginning of the 20th cen-
tury by distinguished Italian chemist Mario Betti via a
modified Mannich reaction named the Betti reaction.[8]
This reaction provides the synthesis of 1-(α-aminoalkyl)-
Appl Organomet Chem. 2021;e6316.
wileyonlinelibrary.com/journal/aoc
© 2021 John Wiley & Sons, Ltd.
1 of 10
https://doi.org/10.1002/aoc.6316

2 of 10
KERI ET AL.
2-naphthols (Betti bases, Figure 1) from β-naphthol,
aldehyde, and ammonia or urea in an ethanolic solution
of potassium hydroxide in two steps for a long time
(9–36 h).[9,10]
consists appropriate amount of silica and alumina. It
belongs to the pentasil family of zeolites with smaller
crystal size and higher surface area showing improved
catalytic activity and selectivity.[44] Its chemical formula,
NanAlnSi96–nO192Á6H2O, shows the unit cell composition
of the zeolite. The existence of aluminum and Si/Al ratio
of ZSM-5 catalyst causes to possess acidic property.[45]
This property makes the catalyst to function as catalyst
support, adsorbent, and so forth. Also, it possesses many
advantages such as excellent solubility in different sol-
vents, high reactivity, easy handling, low cost, and eco-
friendly nature. Because of these features, ZSM-5 has
been used as a catalyst in organic transformations.[46]
Therefore, considering the wide range biological
applications of Betti bases and the unique properties of
ZSM-5 as an ideal catalyst. As a part of our program
aiming at developing an efficient and environmentally
friendly catalytic system for common organic
transformations,[47–50] herein we to report an efficient,
simple, and modified Mannich-type synthesis of Betti
bases or 1-(α-aminoalkyl)-2-naphthols from 2-naphthol,
aromatic aldehydes and different aliphatic amines
(cyclic) using H-ZSM-5 zeolite as catalyst (10 mol%) at
room temperature in quantitative yield (Scheme 1).
Recently, the importance of Betti bases is well
established in pharmaceutical chemistry because of their
bioactivities, including antibacterial,[11,12] antifungal,[13]
anti-inflammatory,[14] anticancer,[15] antitubercular,[16,17]
antitumor,[18,19] fungicidal,[20,21] hypotensive,[22] and
bradycardiac activities (Figure 2).[23] Also, the literature
reveals that the Betti bases are valuable ligands for
transition metals in asymmetric synthesis,[24–26] chiral
auxiliaries for the synthesis of α-amino phosphonic
acids,[27,28] chiral shift reagents for carboxylic acids,[29]
and intermediates in the synthesis of heterocycles.[22,30,31]
Owing to the wide variety of applications of the Betti
bases as building blocks, it is paramount to build up syn-
thetic strategies around this nucleus. Therefore, the vast
range of biological effects associated with this scaffold
has resulted in the Betti bases ring system being
considered as a privileged structure.
Therefore, the synthesis of this core has received
increasing attention to synthetic organic chemists and
biologists. Recently, several methodologies and green
procedures for the synthesis of Betti reactions have also
been successfully developed using catalysts such as
Brønsted and Lewis acids such as SnCl4.5H2O,[32] ionic
liquids,[33] nano-sulfated zirconia,[34] ZrO (OTf)2,[35]
polymer-supported sulfonic acid,[36] Bi (NO3)3.5H2O,[37]
[HMIM]C (CN)3,[38] nanocrystalline MgO,[39] supported
copper triflate,[40] ZnCl2,[41] GO-MnO2-Au ternary
nanocomposite,[42] and sulfated polyborate.[43] Although
these methods/reactions have their advantages, there are
demerits such as the use of expensive low selectivity cata-
lysts, harsh reaction conditions, expensive reagents, mois-
ture sensitivity, toxic solvent/reagents, the use of excess
or stoichiometric amounts of reagents, non-recoverability
of the catalysts, and/or recoverable with tedious separa-
tion procedures, involving lots of toxic waste generation
besides a long reaction time and low yield of the desired
product. To overcome these problems, a general efficient
methodology is needed utilizing zeolite socony mobil-5
(ZSM-5) as an inexpensive and benign catalyst, which
2 | RESULTS AND DISCUSSION
Initially, a model reaction was conducted comprising
three components, 2- naphthol (1), benzaldehyde (2a),
and pyrrolidine (3a) to form 4a to optimize the reaction
conditions with varying solvent and best ideal catalytic
system loading as these are the important parameters,
which affect the yield of the desired product to a great
extent (Table 1). For optimization of the reaction, we
have screened various catalysts and solvents (Table 1,
Entries 1–8) along with H-ZSM-5 zeolite as a catalyst. To
find out the best, eco-friendly, and efficient catalyst for
this reaction, we performed the same reaction with vari-
ous catalysts such as SiO2, TiO2–SiO2, BF3.SiO2, PTA,
TiO2, ZrO2, TiO2–ZrO2, and H-ZSM-5 (Table 1). We
observed that the best results were obtained using cata-
lyst H-ZSM-5 zeolite in terms of product yield and reac-
tion time (Table 1, Entries 13 and 14). To study the real
efficacy of the catalyst for Betti base synthesis, a blank
reaction was carried out in absence of catalyst at room
temperature (r.t.) without keeping in inert condition. We
found that low yield of Betti base was obtained without
catalyst even after keeping the reaction for 12 h at
r.t. (Table 1, Entry 15). Further, we studied the effect of
various organic solvents for the synthesis of Betti base to
increase the product yield. Various conventional organic
solvents, such as MeOH, EtOH, THF, and DCM afforded
FIGURE 1 General structural representation of Betti bases

KERI ET AL.
3 of 10
FIGURE 2 Biologically active Betti bases
SCHEME 1 Synthesis of Betti bases using
ZSM-5 zeolite catalyst
moderate to good yields at r.t. (Table 1, 39%–92%, Entries
8–15). Among all these entries, best results were obtained
using zeolite catalyst at r.t. in benzene and DCM solvents
to the corresponding products in 89% and 91% yield
within 2 h (Table 1, Entries 13 and 14), respectively. It is
worth mentioning that the reaction works efficiently at
ambient conditions so there is no need to carry out the
trial in an inert atmosphere. After finding the ideal cata-
lyst and solvent system, we have investigated the effect of
different amounts of catalyst loading for this transforma-
tion. To find out the suitable catalyst amount loading, a
model reaction was performed using 5 and 20 mol% of H-
ZSM-5 zeolite as a catalyst at r.t. in DCM (Table 1,
Entries 16 and 17). We found that the best results with
10 mol% of catalyst loading resulted in an excellent yield
of 92% in minimum duration of time. The use of a higher
amount of catalysts (20 mol%) neither improves the yield
nor reaction time. So 10 mol% of the catalyst was found
to be the best condition to carry out the reaction.
With the optimized conditions in hand (Table 1,
Entry 14), the scope of the reaction was investigated con-
sidering the nature of the various cyclic amines (five- and
six-membered), functionalized aromatic aldehydes,
and 2-naphthol, allowing access to a library of substituted
amino arylnaphthols (Table 2, Entries 1–20). A wide
range of aromatic aldehydes with substituents at the
ortho, meta, or para-positions were treated with
pyrrolidine and 2-naphthol under the optimized condi-
tion to obtain a good yield of the product (Table 2,
Entries 1–5). It was revealed that all the reactions were
completed efficiently within 2 h, and the expected prod-
ucts were obtained in good to excellent yields (76%–92%).
Variety of substituted benzaldehyde were also success-
fully treated with different aliphatic cyclic amines such
as piperidine, morpholine, and 2-naphthol giving rise to
corresponding products within 1–2 h in 76%–92% yields.
Several electron-releasing or electron-withdrawing sub-
stituents at the ortho, meta, and para-positions of aro-
matic aldehydes showed no significant effect on product
yield and reaction time. However, aromatic aldehydes
bearing groups like ÀNO2, ÀOMe, and ÀCl also dis-
played better reactivity and gives convincible yields. Simi-
larly, we have also tried to attempt the reaction with
proline and hydroxyl proline (Table 2, Entries 19 and 20)
under optimized conditions, but no corresponding Betti
base was obtained. Also, the model reaction was scalable
up to 10 g with mechanical overhead stirring resulted in
the formation of the desired product. On the other hand,
the applicability of this protocol on aliphatic/hetero-
aromatic aldehydes with amines (aliphatic/cyclic) is
under progress. Further, the application of this protocol
for the synthesis of natural products and different drugs
is targeted to be dealt considering the optimized condi-
tions. The spectral data and melting point of the synthe-
sized compounds are in agreement with literature
data (supporting information). Additionally, a single
X-ray crystallographic study was conducted and the
molecular structure of compounds 4a (CCDC 2063270)
and 4b (CCDC 2063272) was unambiguously established
(Figure 3).

4 of 10
KERI ET AL.
TABLE 1 Results of optimization studies for the synthesis of Betti bases
Entry
1
Catalyst
Phosphotungestic acid (PTA)
TiO2
Amount of catalyst (mol% or g)
Solvents
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
Toluene
MeOH
EtOH
Time (h)a
Yield(%)b
0.250
Overnight
49
51
54
59
61
57
41
73
46
54
39
71
89
92
41
73
91
2
0.250
12
12
12
12
12
12
5
3
ZrO2
0.250
4
TiO2-ZrO2
SiO2
0.250
5
10 mol%
10 mol%
10 mol%
0.250
6
TiO2-SiO2
BF3-SiO2
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
H-ZSM-5
7
8
9
10 mol%
10 mol%
10 mol %
10 mol%
10 mol%
10 mol%
8
10
11
12
13
14
15
16
17
9
THF
11
6
CH3CN
Benzene
DCM
2
2
—
12
5 mol%
DCM
20 mol%
DCM
Note: Reaction conditions: Benzaldehyde/pyrrolidine/2–naphthol = 1.2:1.0:1.0, with H–ZSM–5 zeolite catalyst at room temperature. At these reaction
conditions (in bold), the product gives good yields.
aReaction is monitored by TLC.
bIsolated yield.
To obtain the solid-state bonding and special
connectivity information of these amino arylnaphthols
was analyzed by single-crystal X-ray diffraction tech-
nique. Molecular structure of compounds 4a and 4b is
shown in Figure 3. The details of single-crystal data
and structure refinement details of both the com-
pounds are given in Tables S1 and S2. The X-ray
diffraction analysis reveals that both the compounds
are structurally intact, and the naphthol ring is almost
planar concerning the aromatic benzene. The five-
membered pyrrolidine ring of the compounds 4a and
4b is stabilized by a strong intramolecular O—N bond-
ing with a bond distance of 2.591 and 2.606 Å, respec-
tively. Selected bond length, bond angle, and torsional
angle of the compounds 4a and 4b are tabulated in
Tables S3 and S4.
2.1 | Catalyst recyclability studies
From an economic and industrial perspective, succes-
sive recovery and reusability of the catalysts are the
foremost important aspects. Therefore, the reusability
of the catalyst in the model reaction under optimized
reaction conditions was evaluated. After completion of
the reaction, as indicated by TLC, the catalyst was
removed and recovered by filtration under suction
from the reaction mixture. Further, it was attempted
to investigate the reusability of the H-ZSM-5 zeolite
catalyst more than three times. After the first run
of the reaction, a 92% yield was obtained and then
the catalyst was recovered by filtration and dried in
the oven overnight at 120ꢀC. The recovered catalyst
was dried again under vacuum for 12 h and used

KERI ET AL.
5 of 10
TABLE 2 Synthesis of varied aminoalkyl naphthol derivatives via Scheme 1
Entry
Aldehyde
Amine
Product
Product No.
4a
Time (hr)
% Yielda
92
1
2
2
4b
1.3
89
3
4c
2
83
4
5
4d
4e
1.5
81
85
2
6
4f
2
86
7
4g
1.5
81
(Continues)

6 of 10
KERI ET AL.
TABLE 2 (Continued)
Entry
Aldehyde
Amine
Product
Product No.
4h
Time (hr)
% Yielda
8
2
79
9
4i
2
83
10
4j
1.3
79
11
4k
2
76
12
4l
2
85
13
4m
2
83
14
4n
2
81

KERI ET AL.
7 of 10
TABLE 2 (Continued)
Entry
Aldehyde
Amine
Product
Product No.
4o
Time (hr)
% Yielda
79
15
2
16
4p
1.3
87
17
18
4q
1.3
1.3
83
81
4r
19
20
No reaction
4s
4t
12
12
–––
No reaction
–––––
Note: Reaction conditions: Benzaldehydes/alicyclic amine/2-naphthol = 1.2:1.0:1.0, with H–ZSM–5 (10 mol%) catalyst at room temperature.
aIsolated yield.
up to three more runs for the reaction. It was revealed
that after recovering and reuse of the catalyst
displays a minimal decrease in yields without loss
of catalytic activity. The product 4a was obtained in
92%, 87%, 82%, and 73% yields after three runs
(Table 3, Entries 1–4), thus proving the catalyst
recyclability.
2.2 | Exploration of the possible
mechanism
The mechanism of this multi-component reaction
involves the mechanism similar to that of Michael addi-
tion/Knoevenagel condensation cascade process.[51]
A
tentative mechanism for the H-ZSM-5 zeolite-catalyzed

8 of 10
KERI ET AL.
FIGURE 3 Molecular structure of
compounds 4a and 4b
TABLE 3 The recycle study of H-ZSM-5 zeolite for Betti base
found that the formation of imine intermediate is likely
the rate-determining step. H-ZSM-5 is an acidic catalyst
that provides efficient acidic sites to form a coordinate
bond between oxygen atom (or nitrogen atom) which can
activate the formation of imine intermediate, followed by
facilitating the nucleophilic addition.[52]
synthesis
Entry
Recycle study
I run
%Yield (isolated)
1
2
3
4
92
87
82
73
II run
III run
IV run
3 | CONCLUSIONS
In summary, we have developed a new efficient method
for the synthesis of a series of Betti base via Mannich
approach using H-ZSM-5 zeolite as a heterogeneous cata-
lyst in a one-pot reaction, by reacting readily available
different amines, substituted aromatic aldehydes, and
2-naphthol at r.t. Reaction condition was optimized by
studying the effect of catalyst, the effect of solvent, and
varying reaction temperatures for the synthesis of Betti
bases. The noteworthy advantages of this protocol are
(a) high yields with short reaction time; (b) a wide range
of substrate scope using aromatic aldehydes and cyclic
amines (wide substrate compatibility); (c) great activity,
easy separation using cheap catalyst in comparison with
many other catalysts used for the synthesis of Betti bases;
(d) easy work-up procedure (clean reaction profile) and
cost efficiency; and (e) reactions at r.t. Altogether, the
present method is a useful and attractive strategy for
the preparation of different Betti base (1-(α-aminoalkyl)-
2-naphthol) derivatives simply by varying different
substrates.
SCHEME 2 Proposed mechanism for the synthesis Betti base
using H-ZSM-5 catalyst
Betti base synthesis is proposed in Scheme 2. First,
H-ZSM-5 coordinates to benzaldehyde and generates the
ZSM-5-aldehyde intermediate (I), which reacts with
aniline to generate the imine intermediate (II) with the
removal of water and catalyst. In the next step, the imine
intermediate is activated when H-ZSM-5 binds to the
nitrogen (III), which promotes the following nucleo-
philic addition of β-naphthol to give the desired product
(IV) and regenerates H-ZSM-5. From literature, it is
4 | EXPERIMENT
4.1 | Material and methods
Analytical grade reagents were purchased from Sigma-
Aldrich or Fluka or Acros were used as supplied. The

KERI ET AL.
9 of 10
melting points of the products were determined by
Srinivasa Budagumpi https://orcid.org/0000-0001-
6591-7811
1
open capillaries and are uncorrected. The H and 13C
nuclear magnetic resonance (NMR) spectra were
recorded on Bruker AVANCE III spectrometers at
300 and 400 MHz, respectively. Chemical shifts (δ) are
reported in ppm from the standard internal reference
tetramethylsilane (TMS). The following abbreviations
are used: s = singlet, d = doublet, t = triplet, and
m = multiplet. The homogeneity of the compounds was
described by TLC on aluminum silica gel 60 F254
(Merck) detected by ultraviolet (UV) light (254 nm) and
iodine vapors. The catalysts were characterized by
various analytical techniques.
Balappa S. Sasidhar https://orcid.org/0000-0003-1546-
2083
REFERENCES
[1] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley,
Weinheim 2005.
[2] I. Ugi, Pure Appl. Chem. 2001, 73, 187.
[3] B. M. Trost, Angew. Chem. Int. Ed. 1995, 34, 259.
[4] R. S. Keri, K. M. Hosamani, Monatsh. Chem. 2010, 141, 883.
[5] A. Domling, I. Ugi, Angew. Chem. Int. Ed. 2000, 39, 3168.
[6] E. Vicente-Garcia, R. Rosario, S. Preciado, R. Lavilla, Beilstein
J. Org. Chem. 2011, 7, 980.
[7] B. Ganem, Acc. Chem. Res. 2009, 42, 463.
[8] M. Betti, Organic Synth. 1929, 9, 60.
[9] M. Betti, Gazz. Chim. Ital. 1901, 31, 191.
4.2 | General procedure for the synthesis
of the Betti base 4(a-t)
[10] M. Betti, in Organic Syntheses Collective, (Ed: H. Gilman)
Vol. I, 381, John Wiley & Sons, New York 1941.
[11] P. G. Gomez, H. P. Pabon, M. A. Carvajal, J. M. Rincon, Rev
Colomb Cienc Quim. Farm. 1985, 8, 15.
[12] K. Waisser, K. Gregor, L. Kubicova, V. Klimesova, J. Kunes,
M. Machacek, J. Kaustova, Eur. J. Med. Chem. 2000, 35, 733.
[13] K. Gong, H. Wang, X. Ren, Y. Wang, J. Chen, Green Chem.
2015, 17, 3141.
A mixture of 2-naphthol (1.0 eq.), cyclic amine (1.0 eq.),
and benzaldehyde (1.2 eq.) was dissolved in DCM and
stirred at r.t. in the presence of 10 mol% of catalyst within
appropriate time as shown in Table 2. After completion
of reaction, as indicated by TLC, the catalyst was
removed and recovered by filtration from the reaction
mixture and the filtrate solution was concentrated using
rotary evaporator to get crude product and then purified
through the silica gel column chromatography to obtain
corresponding Betti base in excellent yield as indicated in
Table 2.
[14] J. W. Collet, K. Ackermans, J. Lambregts, B. U. Maes, R. V.
Orru, E. Ruijter, J. Org. Chem. 2018, 83, 854.
ꢀ
[15] L. M. Aguirre-Díaz, F. Gandara, M. Iglesias, N. Snejko, E.
ꢀ
Gutiérrez-Puebla, M. A. Monge, J. Am. Chem. Soc. 2015, 137,
6132.
[16] B. P. Mathew, A. Kumar, S. Sharma, P. K. Shukla, M. Nath,
Eur. J. Med. Chem. 2010, 45, 1502.
ꢀ
ꢀ
ꢀ
[17] E. Petrlíkova, K. Waisser, H. Divišova, P. Husakova, P.
ꢀ
ꢀ
Vrabcova, J. Kuneš, K. Kolař, J. Stolaříkova, Bioorg. Med.
Chem. 2010, 18, 8178.
ACKNOWLEDGMENTS
We are grateful to the Jain University, Bangalore, for
financial support. We also thank Nanomission (SR/NM/
NS-20/2014).
[18] J. B. Chylinska, T. Urbanski, M. Mordarski, J. Med. Chem.
1963, 6, 484.
[19] L. Benameur, Z. Bouaziz, P. Nebois, M. H. Bartoli, M. Boitard,
H. Fillion, Chem. Pharm. Bull. 1996, 44, 605.
[20] Z. Bouaziz, J. Riondel, A. Mey, M. Berlion, J. Villard, H.
Filliond, Eur. J. Med. Chem. 1991, 26, 469.
[21] S. B. Arthington, A. M. Motley, D. W. Warnock, C. J.
Morrison, J. Clin. Microbiol. 2000, 38, 2254.
[22] I. Szatmari, A. Hetenyi, L. Lazar, F. Fulop, J. Heterocyclic
Chem. 2004, 41, 367.
AUTHOR CONTRIBUTIONS
Rangappa S. Keri: Funding acquisition; methodology;
project administration; supervision. Mahadeo Patil:
Conceptualization;
methodology.
Srinivasa
Budagumpi: Data curation. Sasidhar B. S.: Formal
analysis.
[23] M. Heydenreich, A. Koch, S. Klod, I. Szatmari, F. Fulop, E.
Kleinpeter, Tetrahedron 2006, 62, 11081.
[24] C. Cardellicchio, M. A. M. Capozzi, F. Naso, Tetrahedron:
Asymmetry 2010, 21, 507.
CONFLICT OF INTEREST
There is are conflicts to declare.
[25] J. Lu, X. Xu, C. Wang, J. He, Y. Hu, H. Hu, Tetrahedron Lett.
2003, 43, 8367.
DATA AVAILABILITY STATEMENT
[26] A. Olyaei, M. Sadeghpour, RSC Adv. 2019, 9, 18467.
[27] J. Feng, S. Dastgir, C. J. Li, Tetrahedron Lett. 2008, 49, 668.
[28] J. Feng, D. S. Bohle, C. J. Li, Tetrahedron: Asymmetry 2007, 18,
1043.
[29] W. Wang, F. Ma, X. Shen, C. Zhang, Tetrahedron: Asymmetry
2007, 18, 832.
The data that support the findings of this study are
available in the supporting information of this article.
ORCID
Rangappa S. Keri https://orcid.org/0000-0001-6262-
8379
Mahadeo Patil https://orcid.org/0000-0002-1558-1675
[30] P. F. Kaiser, J. M. White, C. A. Hutton, J. Am. Chem. Soc.
2008, 130, 16450.

10 of 10
KERI ET AL.
[31] S. G. Mansouri, H. Zali-Boeini, K. Zomorodian, B. Khalvati, R.
Helali Pargali, A. Dehshahri, H. AmiriRudbari, M. Sahihi, Z.
Chavoshpour, Arab. J. Chem. 2020, 13, 1271.
[32] J. Safari, Z. Zarnegar, J. Mol. Catal. A: Chem. A 2013, 379, 269.
[33] A. R. Hajipour, Y. Ghayeb, N. Sheikhan, A. E. Ruoho, Tetrahe-
dron Lett. 2009, 50, 5649.
[47] M. Shanshak, B. Budagumpi, J. G. Małecki, R. S. Keri, Appl.
Organomet. Chem. 2020, 34, e5544.
[48] S. Khan, M. Agasar, A. Ghosh, R. S. Keri, Org. Prep. Proced.
Int. 2019, 51, 153.
[49] M. R. Patil, J. T. Bhanushali, B. M. Nagaraja, R. S. Keri, C.R.
Chimie 2018, 21, 399.
[34] A. Zali, A. Shokrolahi, Chin. Chem. Lett. 2012, 23, 269.
[35] H. Hashemi, A. R. Sardarian, J. Iran. Chem. Soc. 2013, 10, 745.
[36] M. Hajjami, F. Ghorbani, F. Bakhti, Appl. Catal. A 2014,
470, 303.
[50] M. Agasar, M. R. Patil, R. S. Keri, Chem. Data Coll. 2018,
17-18, 178.
[51] P. Heidari, R. Cheraghali, H. Veisi, Appl. Organomet. Chem.
2016, 30, 991.
[37] M. Wang, Y. Liang, T. T. Zhang, J. J. Gao, Chin. Chem. Lett.
2012, 23, 65.
[52] J. Mou, G. Gao, C. Chen, J. Liu, J. Gao, Y. Liu, D. Pei, RSC
Adv. 2017, 7, 13868.
[38] B. Das, K. Laxminarayana, B. Ravikanth, B. R. Rao, J. Mol.
Catal. A 2007, 261, 180.
[39] B. Karmakara, J. Banerji, Tetrahedron Lett. 2011, 52, 4957.
[40] S. D. Dindulkara, V. G. Puranikb, Y. T. Jeong, Tetrahedron
Lett. 2012, 53, 4376.
SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of this
article.
[41] M. K. Foumeshi, A. Z. Halimehjani, H. Paghandeh, P. Beier,
Tetrahedron Lett. 2020, 61, 152270.
[42] P. S. Nayaka, B. Barika, L. Satish, K. Acharya, A. Kumarb, P.
Dasha, Mol. Cat. 2019, 474, 110415.
[43] M. S. Patil, C. K. Khatri, G. U. Chaturbhuj, Monatsh. Chem.
2018, 149, 1453.
[44] R. Van, J. L. Sotelo, J. M. Menéndez, J. A. Melero, Mesopor.
Mater. 2000, 39, 135.
How to cite this article: R. S. Keri, M. Patil,
S. Budagumpi, B. S. Sasidhar, Appl Organomet
Chem 2021, e6316. https://doi.org/10.1002/aoc.
6316
[45] R. Lu, H. Tangho, Q. Wang, S. Xiang, J. Nat. Gas Chem. 2003,
12, 56.
[46] A. R. Massah, R. J. Kalbasi, A. Shafiei, Monatsh. Chem. 2012,
143, 643.