Copper(I)-Catalyzed Oxidative Coupling between 2‑Aminobenzothiazole and Terminal Alkyne: Formation of Benzothiazine

An unprecedented formation of benzothiazine during copper(I)-catalyzed oxidative coupling of 2-aminobenzothiazole and terminal alkyne in air has been observed. This unique transformation possibly occurs through the ring opening of 2-aminobenzothiazole and subsequent oxidative coupling with alkyne fo...

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Bibliographic Details
Published in:Organic letters 2014-11, Vol.16 (21), p.5652-5655
Main Authors: Mitra, Shubhanjan, Chakraborty, Amrita, Mishra, Subhajit, Majee, Adinath, Hajra, Alakananda
Format: Article
Language:English
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Summary:An unprecedented formation of benzothiazine during copper(I)-catalyzed oxidative coupling of 2-aminobenzothiazole and terminal alkyne in air has been observed. This unique transformation possibly occurs through the ring opening of 2-aminobenzothiazole and subsequent oxidative coupling with alkyne followed by intramolecular cyclization. A variety of substituted benzo[b][1,4]thiazine-4-carbonitriles are obtained by this protocol.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502729c