Facial synthesis of novel 3-(2-methylbenzofuran-3-yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazole-1-yl)methyl)-1,2,4-oxadiazole derivatives

Article abstract of DOI:10.1080/00397911.2021.1884881

An efficient and practical methodology was developed for rapid and green synthesis of novel benzofuran-1,2,4-oxadiazole-1,2,3-triazole hybrids (6a–n) from 5-(chloromethyl)-3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles (4a–b) by in situ generation of 5-(az

Full text of DOI:10.1080/00397911.2021.1884881

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Facial synthesis of novel 3-(2-methylbenzofuran-3-
yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazole-1-
yl)methyl)-1,2,4-oxadiazole derivatives
Jagram Anterbedy, Sudhakar Mokenapelli & Gangadhar Thalari
To cite this article: Jagram Anterbedy, Sudhakar Mokenapelli & Gangadhar Thalari (2021)
Facial synthesis of novel 3-(2-methylbenzofuran-3-yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazole-1-
yl)methyl)-1,2,4-oxadiazole derivatives, Synthetic Communications, 51:9, 1417-1424, DOI:
10.1080/00397911.2021.1884881
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SYNTHETIC COMMUNICATIONSV
2021, VOL. 51, NO. 9, 1417–1424
https://doi.org/10.1080/00397911.2021.1884881
Facial synthesis of novel 3-(2-methylbenzofuran-3-yl)-5-((4-
(phenoxymethyl)-1H-1,2,3-triazole-1-yl)methyl)-1,2,4-
oxadiazole derivatives
Jagram Anterbedy, Sudhakar Mokenapelli , and Gangadhar Thalari
Natural Products Laboratory, Department of Chemistry, University College of Science, Osmania
University, Hyderabad, India
ABSTRACT
ARTICLE HISTORY
Received 25 October 2020
An efficient and practical methodology was developed for rapid and
green synthesis of novel benzofuran-1,2,4-oxadiazole-1,2,3-triazole
hybrids (6a–n) from 5-(chloromethyl)-3-(2-methylbenzofuran-3-yl)-
1,2,4-oxadiazoles (4a–b) by in situ generation of 5-(azidomethyl)-3-(2-
methylbenzofuran-3-yl)-1,2,4-oxadiazoles followed by 1,3-dipolar
cycloaddition with substituted-1-(prop-2-yn-1-yloxy)benzenes (5a–g)
through Click reaction under mild reaction conditions with good to
excellent yields (70–86%).
KEYWORDS
Benzofuran; click reaction;
1,3-dipolar cycloaddition;
1,2,4-oxadiazole;
1,2,3-triazole
GRAPHICAL ABSTRACT
Introduction
Benzofuran motifs have significant molecules from the last decades attributable to their
attentive physiological and chemotherapeutic properties along with their widespread
amount in nature.[1] The derivatives of benzofuran containing compounds are signifi-
cantly distributed in nature and exhibiting physiological and chemotherapeutic proper-
ties like anti-hyperglycemic,[2] analgesic,[3] anti-parasitic,[4] anti-microbial,[5] anti-tumor
and kinase inhibitor activities.[6,7] Especially benzofurans with substituents at C-2 and
C-3 positions have been widely investigated for selective biological and pharmacological
properties.[8,9] Recently, benzofuran containing drugs were accepted in U.S. FDA.[10,11]
Benzofuran derivatives are innovative biodynamic agents that can be used to design and
development of novel potential therapeutic agents for diverse biological activities.[12]
1,2,4-oxadiazoles are promising frameworks of biologically active natural products.[13]
The various 3,5 disubsttituted oxadiazole derivatives were reported as anti-cancer,[14]
anti-biotic,[15] anti-fungal,[16] anti-oxidant,[17] anti-inflammatory[18] and anti-convulsant
CONTACT Gangadhar Thalari
gangadharchemou@gmail.com
Natural Products Laboratory, Department of
Chemistry, University College of Science, Osmania University, Tarnaka, Hyderabad 500007 India.
Supplemental data for this article can be accessed on the publisher’s website
ß 2021 Taylor & Francis Group, LLC

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J. ANTERBEDY ET AL.
agents.[19] Recently, various 3,5-disubstituted-1,2,4-oxadiazoles were reported as poten-
tial anti-cancer agents and apoptosis against various cancer cell lines.[20–24] Furthermore
1,2,4-oxadiazole derivatives are possess hydrolytic, metabolic stability, improved phar-
macokinetic properties[25] and also defined as bioisosters of amides and esters.[26] 1,2,3-
Triazoles have been established as significant molecules in medicinal chemistry in last
decades. 1,2,3-Triazole moiety does not occur in nature although, the basic 1,4-disubsti-
tuted-1,2,3-triazole ring itself is a potential pharmacophore that showed interesting bio-
logical activities such as anti-bacterial,[27] anti-malarial,[28] anti-fungal,[29] anti-viral,[30]
anti-tubercular[31] and anti-cancer activities.[32] 1,2,3-Triazoles can actively involve in
dipole-dipole and p-stacking interactions and hydrogen bonding with enhanced binding
affinity to target proteins,[33–35] these are considered as peptide and amide bond iso-
steres.[36,37] Sharpless et al. reported[38] the Cu (I) catalyzed 1,3-dipolar cycloaddition
between terminal alkynes and alkyl azides leads regioselectively 1,4-disubstituted-1,2,3-
triazoles under Click reaction condition. Furthermore, one-pot 1,3-cycloaddition was
earlier reported[39,40] Feldmanin et al. were reported situ azide generated cycloadd-
ition,[41] Pokhodylo et al. were reported one-pot 1,2,3-triazol and 1,3,4/1,2,4-oxadiazole
hybrids.[42] Hybrid molecules with two or more diverse heterocyclic pharmacophores
having significant results in drug discovery, due to reduce side effects and overcome the
drug resistance may also precise action mechanisms.[43,44] Notably heterocyclic hybrids
were privileged scaffolds exhibiting several biological activities such as anti-fungal, anti-
tuberculosis, anti-malarial, anti-inflammatory, anti-cancer and anti-bacterial activ-
ity.[45,46] Recently, various oxygen and nitrogen-containing heterocyclic pharmacophores
with 1,2,3-triazole linker were found in the development of novel anti-cancer drugs.[47]
These fascinating biological properties enhance our interest toward the synthesis of oxa-
diazole, 1,2,3-triazole derivatives and their biological activity.
Results and discussion
Novel benzofuran-1,2,4-oxadiazole-1,2,3-triazole hybrids (6a–n) were synthesized from
2H-chromene-3-carbonitriles (1a–b). 2H-chromene-3-carbonitriles (1a–b) were synthe-
sized from the previous reported procedure.[48] Initially, 5-(chloromethyl)-3-(2-methyl-
benzofuran-3-yl)-1,2,4-oxadiazoles (4a–b) were prepared from 2H-chromene-3-
carbonitriles (1a-b) by using my earlier reported method.[49] Catalyst free sodium azide
mediated ring retrenchment in pyran ring of compounds 1(a–b) into furan ring in
DMSO at 160 ꢀC witch gave 2-methylbenzofuran-3-carbonitriles (2a–b), were respect-
ively. Furthermore, hydroxylamine hydrochloride reacted with compounds 2(a–b) using
triethylamine in ethanol under reflux gave N-hydroxy-2-methylbenzofuran-3-carboximi-
damides (3a–b) individually. Moreover, compounds 3(a–b) was acetylation followed by
condensation with chloroacetyl chloride in THF at reflux, provided 5-(chloromethyl)-3-
(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles (4a–b) respectively (Scheme 1).
Compounds 4(a–b) were treated with sodium azide provided, in situ 5-(azido-
methyl)-3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles subsequently, 1,3-dipolar cyclo-
addition with substituted-1-(prop-2-yn-1-yloxy)benzenes (5a–g) using sodium
ascorbate and CuSO4.5H2O in DMF:H2O (7:3) under Click reaction gave corresponding

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Scheme 1. Synthesis of compounds 4(a–b), reagents and conditions: (i) NaN3, DMSO, 160 ꢀC, 30 min;
(i) NH2OH.HCl, TEA, EtOH, reflux, 6 h; (iii) Chloroacetylchloride, THF, reflux, 6 h.
Scheme 2. Synthesis of compounds 6(a–n), reagents and conditions: (i) (a) NaN3, DMF:H2O (7:3),
70 ꢀC, 1 h; (b) Sodium ascorbate, CuSO4.5H2O, rt, 1 h.
3-(2-methylbenzofuran-3-yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazole-1-yl)methyl)-1,2,4-
oxadiazole derivatives (6a–n) with good yields (Scheme 2; Table 1).
Conclusion
In conclusion, we established an efficient methodology for rapid and green synthesis of
novel benzofuran-1,2,4-oxadiazole-1,2,3-triazole hybrids (6a–n) from 5-(chloromethyl)-
3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles (4a–b) by in situ construction of

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J. ANTERBEDY ET AL.
Table
1. Synthesis
of
3-(2-methylbenzofuran-3-yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazole-1-
yl)methyl)-1,2,4-oxadiazole derivatives (6a–n).
Entry
Product
Yield (%)
80
mp (ꢀC)
6a
220–222
6b
6c
6d
78
82
76
217–219
214–216
221–223
6e
6f
79
83
70
82
224–226
228–230
213–215
213–215
6g
6h
6i
82
85
79
210–212
216–218
224–226
6j
6k
(continued)

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Table 1. Continued.
Entry
Product
Yield (%)
mp (ꢀC)
6l
86
227–229
6m
6n
80
229–231
223–225
74
5-(azidomethyl)-3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazoles followed by 1,3-dipolar
cycloaddition with substituted-1-(prop-2-yn-1-yloxy)benzenes (5a–g) through Click
reaction using DMF:H2O (7:3). The reaction, with this catalyst was carried out under
mild reaction conditions with good to excellent yields (70–86%). Further studies aimed
at broadening the panel of application of these highly stable, active, inexpensive, hetero-
geneous and easily prepared heterogeneous metal catalysts are in progress.
General experimental methods
All solvents and reagents were obtained from commercial suppliers. All reactions were
performed under nitrogen atmosphere unless otherwise noted. Column chromatography
1
was performed using Merck silica gel 60–120 mesh. H NMR and 13C NMR spectra
were recorded on bruker spectrometer at 400 MHz and 101 MHz, tetramethylsilane
(TMS) as internal standard, chemical shift (d) are reported in parts per million (ppm).
Multiplicity (singlet (s), doublet (d), doublet of doublet (dd), triplet of doublet (td) and
multiplet (m)) coupling constant (J in Hz). Mass spectral analysis was accomplished
using electro spray ionization (ESI) techniques.
General procedure for synthesis of 3-(2-methylbenzofuran-3-yl)-5-((4-
(phenoxymethyl)-1H-1,2,3-triazol-1-yl)methyl)-1,2,4-oxadiazole derivatives (6a–n)
Sodium azide (0.043 g, 0.663 mmol) was added to a stirred solution of 5-(chloromethyl)-
3-(2-methylbenzofuran-3-yl)-1,2,4-oxadiazole (4a) (0.150 g, 0.603 mmol) in 5 mL of
DMF: H2O (7:3) stirred 70 ꢀC for 1 h. The progress of reaction was monitored by TLC.
After the completion of the reaction, reaction mixture was cooled to room temperature
then add (prop-2-yn-1-yloxy)benzene (5a) (0.079 g, 0.603 mmol), sodium ascorbate
(0.02 mmol) and CuSO4.5H2O (0.02 mmol) at room temperature stirred for 1 h. After
the completion of the reaction. The reaction mixture was poured in ice cold water and
extracted with ethyl acetate. Organic layer was separated and dried over anhydrous

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J. ANTERBEDY ET AL.
Na2SO4 then filtered and evaporated. The crude compound was subjected to column
purification with n-hexane in ethyl acetate (8:2) to yield compound (6a).
3-(2-Methylbenzofuran-3-yl)-5-((4-(phenoxymethyl)-1H-1,2,3-triazol-1-yl)methyl)-1,2,4-
oxadiazole (6a)
1
Yield: 80%, Off white solid, mp: 220–222 ꢀC. H NMR (400 MHz, CDCl3) d 8.07–8.01
(m, 1H), 7.94 (s, 1H), 7.48–7.44 (m, 1H), 7.34–7.27 (m, 4H), 7.02–6.96 (m, 3H), 5.91 (s,
2H), 5.27 (s, 2H), 2.78 (s, 3H). 13C NMR (101 MHz, CDCl3) d 171.17, 164.75, 159.11,
158.07, 154.05, 145.54, 129.62, 125.82, 124.66, 123.75, 123.52, 121.57, 121.42, 114.73,
110.84, 103.79, 61.86, 45.24, 14.33. ESI-HRMS m/z calcd for C21H17N5O3 388.1409
[M þ H]þ, found 388.1404.
Acknowledgments
Authors thank the Head Department of Chemistry and CFRD, Osmania University, Hyderabad,
India for providing laboratory facilities.
ORCID
Sudhakar Mokenapelli
http://orcid.org/0000-0001-9575-4830
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