Green synthesis of novel quinoxaline sulfonamides
with antibacterial activity
Mohammad Hossein Mosslemin
Ahmad Reza Massah
Received: 23 November 2016 / Accepted: 2 February 2017 / Published online: 6 March 2017
Ó Springer Science+Business Media Dordrecht 2017
Abstract A facile and efﬁcient method was investigated for the synthesis of different
quinoxalines by the reaction of o-phenylene diamine and 2-bromoacetophenones.
This procedure was carried out in ethanol under catalyst-free conditions. Several
sulfonamides were synthesized from 2-(4-methoxyphenyl)-quinoxaline in two steps.
At ﬁrst chlorosulfonation of 2-(4-methoxyphenyl) quinoxaline was done using
chlorosulfonic acid and led to 2-methoxy-5-quinoxalin-2-yl-benzenesulfonyl chloride.
Then quinoxaline sulfonamides were synthesized by the reaction of quinoxaline
sulfonyl chloride with different aromatic amines under solvent-free conditions. All the
products were obtained in excellent yields after an easy work-up and were evaluated
for antibacterial activities against Staphylococcus spp. and Escherichia coli bacteria.
Keywords Quinoxaline Á Catalyst-free Á Sulfonamide Á Solvent-free Á Antibacterial
Quinoxalines (QXs) or benzopyrazines and their derivatives are the varied class of
nitrogen-containing heterocyclic compounds, which display various pharmacolog-
ical and biological activities, such as antiviral , antibacterial , antifungal ,
anticancer , and antimalarial [5, 6]. Numerous methods have been reported for
Electronic supplementary material The online version of this article (doi:10.1007/s11164-017-2895-6)
contains supplementary material, which is available to authorized users.
& Ahmad Reza Massah
Department of Chemistry, Shahreza Branch, Islamic Azad University, Shahreza,
Isfahan 311-86145, Iran
Department of Chemistry, Yazd Branch, Islamic Azad University, Yazd 89195-155, Iran
Res Chem Intermed (2017) 43:4549–4559