ARTICLE
An efficient green synthesis and antibacterial activity
of 1,3-benzoxazine and 1,3-naphthoxazine using NaCl.SiO
2
as solid catalyst in neat condition
Putusenla Imchen
1
| Betokali K. Zhimomi
1
| Lensayula Longkumer
1
|
Shokip Tumtin
2
| Toka Swu
3
| Tovishe Phucho
1
1
Department of Chemistry, Nagaland
University, Zunheboto, India
2
Department of Chemistry, Kirori Mal
College, Delhi University, Delhi, India
3
Department of Chemistry, Pondicherry
University, Puducherry, India
Correspondence
Tovishe Phucho, Department of
Chemistry, Nagaland University, Lumami
798627, Zunheboto, Nagaland, India.
Email: itphucho@nagalanduniversity.
ac.in
Funding information
Science and Engineering Research Board,
Grant/Award Number: EEQ/2016/000260
dated 28-02-2017
Abstract
A series of 1,3-oxazine derivatives were synthesized by a one-pot three-
component (ie, phenol, formaldehyde, amine) method where SiO
2
bonded with
NaCl was used as a reusable, more efficient, easily prepared, and available solid
catalyst. The reactions were also carried out at room temperature for greener
approach. in vitro studies for the synthesized compounds were also done
against two gram-positive (Bacillus subtilis and Staphylococcus aureus) and two
gram-negative bacteria (Escherichia coli and Klebsiella pneumonia) to check for
their applicability as an antibacterial agent where some of the synthesized com-
pounds gives the best antibacterial activity against selected bacterial strains.
Streptomycin was used as a standard control for all the microbial test.
1 | INTRODUCTION
Oxazine, due to their wide and diverse range of biological
activities are considered as an important type of heterocycles
and are therefore, a special interest for the synthetic areas.
The 1, 3-oxazine nucleus features prominently in many
biologically important natural products and other bioactive
molecules.
[1–4]
They have gained much importance
due to their many biological activities like antitubular,
[3]
antibacterial,
[4]
anticancer,
[5]
anticonversant,
[2]
and analge-
sic.
[1]
Benzo-1,3-oxazines are also generally known to pos-
sess biologically properties like cytotoxic,, antianginal,
antihypertensive effects, demonstrating antirheumatic, and
antiosteoclastic bone resorption activity.
[6]
Multicomponent reactions (MCRs) have become
highly efficient as they avoid time consumption, has eco-
nomic purification processes, formation of several bonds
in a single step and manufacture of complex molecular
architectures.
[7]
This type of MCRs incorporate synthetic
strategy as the products formed are obtained in just a
single step and also its variation can be simply developed
by changing the reacting components.
[8]
Recently, there is a consideration on the use and
design of environmentally friendly heterogeneous catalysts
to reduce the amount of toxic waste. Among them, nano
scale metal oxides
[9]
have been efficiently used as catalysts
for organic transformations.
[10–12]
Solid-support catalyst
has become prominently important in the recent years as
they are easily available/easily prepared and are generally
less expensive. They can also be easily separated from
reaction mixtures and can be reused which make them
eco-friendly and also simple to use. This is one of the main
reasons why silica-supported catalyst in MCRs has gained
much importance and attention.
[13]
Gabbas et al also syn-
thesized a series of 3,4-dihydro-2H-benzo- and naphtho-
1,3-oxazine derivatives using methylene bromide for ring-
closure reaction where they also confirmed the presence
of antibacterial property in almost all of their synthesized
compounds via in vitro antimicrobial studies.
[14a]
As deriv-
atives containing oxazine ring system have shown to
Received: 10 December 2019 Revised: 27 April 2020 Accepted: 29 May 2020
DOI: 10.1002/jhet.4059
J Heterocyclic Chem. 2020;1–6. wileyonlinelibrary.com/journal/jhet © 2020 Wiley Periodicals LLC. 1