Research Article
Metal-free Catalyzed One-Pot Multicomponent Synthesis of
(E)-3-(2-((5-(Benzylideneamino)-1,3,4-thiadiazol-2-yl)thio)
Acetyl)-2H-chromen-2-one Derivatives and Their
Biological Evaluation
Shivanand Merugu,
1
Vijaya Kumar Ponnamaneni,
2
Ravi Varala,
3
Syed Farooq Adil ,
4
Mujeeb Khan,
4
Mohammed Rafiq H. Siddiqui ,
4
and Ravikumar Vemula
1
1
Department of Chemistry, Kamala Institute of Technology and Science, Huzurabad, Karimnagar 505 468, Telangana, India
2
Synocule Research Labs Private Limited, Plot No. 16, CFC Area, IDA Nacharam, Hyderabad 500 076, Telangana, India
3
Scrips Pharma, Mallapur, Hyderabad 500076, Telangana, India
4
Department of Chemistry, King Saud University, Riyadh 11451, Saudi Arabia
Correspondence should be addressed to Syed Farooq Adil; sfadil@ksu.edu.sa and Ravikumar Vemula; vemularavi97@gmail.com
Received 1 December 2019; Accepted 4 February 2020; Published 10 April 2020
Academic Editor: Andrea Penoni
Copyright © 2020 Shivanand Merugu et al. is is an open access article distributed under the Creative Commons Attribution
License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is
properly cited.
A series of (E)-3-(2-((5-(benzylideneamino)-1,3,4-thiadiazol-2-yl)thio) acetyl)-2H-chromen-2-one and its derivatives (4a-h) have
been obtained using a one-pot multicomponent reaction with good yields. e compounds have been synthesized from 3-(2-
bromoacetyl)chromen-2-ones ( 1), 5-amino-1,3,4-thiadiazole-2-thiol (2), and substituted benzaldehydes (3) in anhydrous ethanol
and conc. H
2
SO
4
. Subsequently, all the synthesized compounds have been screened for their antimicrobial activity and char-
acterized by analytical and spectral data.
1. Introduction
Over the several decades, the interest of the scientific
community in the heterocyclic compounds and their various
derivatives has been persistent due to their broad applica-
tions in pharmaceutical and chemical industries [1]. Among
various heterocyclic compounds such as pyrazole, tetrahy-
droquinoline, and benzotriazole, thiadiazole has gained
prominent importance which consists of an important five-
membered heterocyclic system containing two nitrogen
atoms and a sulfur atom [2]. Particularly, among various
thiadiazole, the 1,3,4,-thiadiazole has been studied more
than any other counterpart, due to its biologically signifi-
cance [3]. e 1,3,4-thiadiazole and most of their derivatives
are important heterocyclic entities in pharmaceutical as well
as in medicinal chemistry, due to their diverse biological
activities as well as inhibition properties against a variety of
specific enzymes [4], several of which are known to possess
excellent antibacterial [5], antimicrobial [4, 6], anti-in-
flammatory [7], anticonvulsant [8], antidepressant and
anxiolytic [9], anti-tuberculosis [10], anticancer [11], and
CNS depressant activities [12]. In this regard, various
coumarin (benzopyran-2-one) derivatives have particularly
shown remarkable biological activities due to their privileged
structure which facilitates high affinity and specificity to
different molecular targets [13]. Besides, the presence of
planar aromatic ring fused with lactone functionality,
availability of highly interactive functional groups which
enhances the interactions with foreign moieties including
proteins makes this heterocycle a unique pharmacophore in
the field of medicinal chemistry.
In view of this importance, the present study focused on
a facile one-pot multicomponent reaction of Schiff base
containing heterocyclics. A multicomponent reaction
Hindawi
Journal of Chemistry
Volume 2020, Article ID 4869279, 7 pages
https://doi.org/10.1155/2020/4869279