Multicomponent synthesis of fully substituted thiazoles using glycine-based dithiocarbamates, acetic anhydride and nitroalkenes.

Reaction of glycine-based dithiocarbamates with nitroalkenes in the presence of acetic anhydride was utilized for the synthesis of fully substituted 2-(alkylsulfanyl)-4-(nitroalkyl)-5-acyloxy-1,3-thiazoles. The reaction proceeds via the in situ formation of thiazol-5(4H)-one from glycine-based dithiocarbamates, followed by the Michael addition of this intermediate to nitroalkenes, aromatization, and esterification reaction cascade. This new one-pot three-component reaction afforded a diverse library of fully substituted thiazoles in high to excellent yields under solvent-free conditions.

Citation

Azim Ziyaei Halimehjani, Maryam Saeb, Maryam Khalesi. Multicomponent synthesis of fully substituted thiazoles using glycine-based dithiocarbamates, acetic anhydride and nitroalkenes. Organic & biomolecular chemistry. 2022 May 11;20(18):3763-3766

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PMID: 35420106

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