TBHP‐Mediated Intermolecular Radical Coupling and Intramolecular Cyclization Cascade: Access to Furo[2,3‐b]quinoxalines and Their Photophysical Study

A cascade one‐pot strategy to construct 31 examples of furo‐fused quinoxalines in up to 88% yields has been devised from readily accessible β‐ketothioamides and quinoxalin‐2‐ones in open flask at room temperature under TBHP mediated conditions. Mechanistic studies revealed that the overall reactivit...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-01, Vol.366 (2), p.262-268
Main Authors: Ray, Subhasish, Kumar, Vipin, Singh, Saurabh, Bandyopadhyay, Krishanu, Saha, Satyen, Shankar Singh, Maya
Format: Article
Language:English
Subjects:
Furo[2,3-b]quinoxalines
Intramolecular Cyclization
Photophysical Studies
Radical Coupling
TBHP-mediated
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A cascade one‐pot strategy to construct 31 examples of furo‐fused quinoxalines in up to 88% yields has been devised from readily accessible β‐ketothioamides and quinoxalin‐2‐ones in open flask at room temperature under TBHP mediated conditions. Mechanistic studies revealed that the overall reactivity relies on the seamless integration of intermolecular radical coupling and intramolecular cyclization via desulfhydration of C=S bond cleavage. Generation of H2S as the only by‐product makes this process highly attractive. Furthermore, the photophysical behavior of the furo‐fused quinoxalines has also been studied.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301045