Open AccessOne-pot protocol for the synthesis of quinoxalines from styrenes, o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine using triiodoisocyanuric acid
Author(s) -
B. Suresh Kuarm,
Marumamula Hanumaiah,
B. Rajitha
Publication year - 2021
Publication title -
organic communications
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.238
H-Index - 15
ISSN - 1307-6175
DOI - 10.25135/acg.oc.93.2009.1800
Subject(s) - quinoxaline , diamine , chemistry , substrate (aquarium) , yield (engineering) , condensation , organic chemistry , o phenylenediamine , condensation reaction , ketone , medicinal chemistry , polymer chemistry , catalysis , materials science , oceanography , physics , metallurgy , thermodynamics , geology
Triiodoisocyanuric acid (TICA) controlled one-pot and easy-operational protocol has been developed for the synthesis of substituted phenylquinoxalines (3a-3i) and phenyl-[1,2,5]thiadiazolo[3,4-f]quinoxaline (5a-5f) from styrenes with o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine respectively. The reaction involves co-bromination and oxidation for the formation of an a-bromo ketone as an intermediate in the presence of triiodoisocyanuric acid, followed by condensation with the o-phenylenediamine and benzo[c][1,2,5]thiadiazole-4,5-diamine for the formation of phenylquinoxalines (3a-3i) and phenyl-[1,2,5]thiadiazolo[3,4-f]quinoxaline (5a-5f) in 55-79% yield. This protocol environmentally benign and economically viable. Substituted quinoxalines were obtained in good to excellent yields with wide substrate scope and functional-group tolerance.