Oxidative Cyclization of 4‐(2‐Mercaptophenyl)‐Substituted 4 H ‐1,2,4‐Triazolium Species to Tricyclic Benzothiazolium Salts

Herein we report a generally applicable method for the preparation of N ‐substituted benzo[4,5]thiazolo[2,3‐ c ][1,2,4]triazol‐1‐ium salts from air stable precursors. This transformation features selective deprotection of a para‐methoxybenzyl protected thiol followed by C−H functionalization of the...

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Bibliographic Details
Published in:European journal of organic chemistry 2022-05, Vol.2022 (20)
Main Authors: Ardón‐Muñoz, Luis G., Bolliger, Jeanne L.
Format: Article
Language:English
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Summary:Herein we report a generally applicable method for the preparation of N ‐substituted benzo[4,5]thiazolo[2,3‐ c ][1,2,4]triazol‐1‐ium salts from air stable precursors. This transformation features selective deprotection of a para‐methoxybenzyl protected thiol followed by C−H functionalization of the linked 1,2,4‐triazolium salts under oxidative conditions. Using this procedure, we synthesized a variety of tricyclic thiazolium salts which contain both electron‐withdrawing and electron‐donating aromatic substituents as well as aliphatic substituents. Our approach also tolerates many functional groups including alkynes, alcohols, diols, amides, and polyethers.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.202200121