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Salicylic Acid‐Promoted Three‐Component Annulation of Benzimidazoles, Aryl Nitroalkenes and Elemental Sulfur
Author(s) -
Mei Ruhuai,
Xiong Feng,
Yang Chenrui,
Zhao Jinwu
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001564
Subject(s) - chemistry , thiazole , aromatization , annulation , combinatorial chemistry , sulfur , aryl , nucleophile , salicylic acid , organic chemistry , catalysis , biochemistry , alkyl
Herein, a three‐component cyclization reaction of benzimidazoles, aryl nitroalkenes and elemental sulfur has been developed. Cheap and easily available salicylic acid found to be an efficient mediator for the present transformation. This protocol provides a facile access to structurally significant imidazo[2,1‐ b ]thiazole skeleton from simple raw materials with a range of compatible synthetically useful functionalities. Furthermore, gram‐scale preparation of this method is effective, which enables potential applications of it in broader fields of molecule synthesis. Mechanistically, a reaction cascade involving sequential aza‐Michael addition, nucleophilic sulfuration, and deaminative aromatization was proposed.