Facile Synthesis of Quinoxaline-2-thiol and Quinoxaline from α-Oxosulfines and o-Arylenediamines

Abstract

A series of quinoxaline-2-thiols and quinoxalines were prepared in moderate to good yields from various phenacyl sulfoxides bearing 1-methyl-1H-tetrazole and o-arylenediamines. The proposed reaction mechanism involves generation of sulfines from the phenacyl sulfoxides bearing 1-methyl-1H-tetrazole through thermolysis elimination. Then, site-selective carbophilic addition of sulfines by o-arylenediamines, followed by elimination, intramolecular nucleophilic addition, and dehydration condensation. The current method provides a direct and simple strategy for the preparation of quinoxaline-2-thiols and quinoxalines.

Key words

α-oxosulfines - o-arylenediamines - quinoxaline-2-thiol - quinoxaline - ring formation reaction

Publication History

Received: 12 November 2021

Accepted after revision: 14 January 2022

Accepted Manuscript online:
14 January 2022

Article published online:
01 March 2022

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