Add time:07/12/2019         Source:sciencedirect.com

Publisher SummaryThis chapter describes the syntheses and reactions of the 5-membered heterocyclic ring systems containing nitrogen and sulfur (or selenium). The Hantzsch reaction is used in the production of thiazoles. This reaction generates one equivalent (equiv.) of hydrogen bromide that can cause significant loss of optical purity with substrates prone to epimerization under original Hantzsch conditions (refluxing ethanol). A series of 2-trifluoromethyl and 2-difluoromethyl substituted benzothiazoles may be synthesized by a one-pot reaction of trifluoroacetic acid and difluoroacetic acid, respectively, with 2–aminobenzenethiol. The chapter also discusses several reactions of thiazoles and fused derivatives. The 5-(tributylstannyl)-2-phenylthiazole may be prepared from 2-phenylthiazole via lithiation and subsequent quenching with Bu3SnCl. The facile and efficient one-pot synthesis of highly substituted isothiazol-3 (2H) ones may be developed using the readily available α-carbamoylketene-S,S-acetals. The chapter discusses the importance of π-rich heterocycles in medicinal chemistry and natural products.

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