Convenient synthesis of 2-chloro-3-substituted quinoxalines by visible-light-induced radical cascade cyclization of ortho -diisocyanoarenes with sulfinic acids

2-Chloro-3-substituted quinoxalines (3) are significant precursors in the synthesis of 2,3-di-unsymmetrically substituted quinoxalines, including quinacillin, which has been shown to be effective against a number of transplantable diseases and cancer cells. Despite the fact that there are two ways t...

Full description

Saved in:
Bibliographic Details
Published in:New journal of chemistry 2024-03, Vol.48 (10), p.4521-4528
Main Authors: Natarajan, Palani, Partigya, Meena
Format: Article
Language:English
Subjects:
High temperature
Quinoxalines
Reaction mechanisms
Reagents
Substitutes
Synthesis
Citations: Items that this one cites
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:2-Chloro-3-substituted quinoxalines (3) are significant precursors in the synthesis of 2,3-di-unsymmetrically substituted quinoxalines, including quinacillin, which has been shown to be effective against a number of transplantable diseases and cancer cells. Despite the fact that there are two ways to produce 2-chloro-3-substituted quinoxalines (3), both procedures are hampered by high temperatures, metal contamination, and toxic reagents. A visible-light-induced radical cascade cyclization of ortho -diisocyanoarenes (1) with alkyl(aryl)sulfinic acids (2) and trichloroisocyanuric acid has been developed. Also, a plausible reaction mechanism and synthetic uses of 2-chloro-3-substituted quinoxalines (3) towards a few 2,3-di-unsymmetrically-substituted quinoxalines have been described. This novel approach easily accesses 2-chloro-3-substituted quinoxalines (3) in good yields, without using elevated temperatures, or metal- or toxic reagents.
ISSN:1144-0546
1369-9261
DOI:10.1039/D3NJ05642B