JOURNAL 1800


Organic Communications
VOLUME & ISSUE
Available Online: January 24,2021
PAGES
p.1 - 10
DOI ADDRESS
http://doi.org/10.25135/acg.oc.93.2009.1800
(DOI number will be activated after the manuscript has been available in an issue.)
STATISTICS
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AUTHORS
  • Rajitha Bavanthula
  • Suresh Kuarm Bowroju
  • Hanumaiah Marumamula
PDF OF ARTICLE

GRAPHICAL ABSTRACT


ABSTRACT


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.

 

 

 

KEYWORDS
  • Quinoxalines
  • one-pot protocol
  • triiodoisocyanuric acid
  • styrenes

SUPPORTING INFORMATION


Supporting Information
Download File 93-OC-2009-1800-SI.pdf (2.84 MB)