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Paper | Special issue | Vol 103, No. 1, 2021, pp.258-266
Published online, 21st May, 2020
DOI: 10.3987/COM-20-S(K)7
■ Synthesis of 5-H Thiazoles via Thioamide Dianions with Thioformamides: Pyridylmethyl Group on the Nitrogen Atom of Thiazole Promotes the Formation of 5-H Thiazoles

Khurnia Krisna Puji Pamungkas , Shizuka Hattori, Toshifumi Maruyama, Masahiro Ebihara, and Toshiaki Murai*

*Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University , 1-1 Yanagido, Gifu, Gifu 501-1193, Japan

Abstract

The reaction of in situ-generated thioamide dianions having a pyridylmethyl group on the nitrogen atom with thioformamides resulted in the formation of 5-H thiazoles as major products along with 5-N,N-dimethylaminothiazoles. The presence of a pyridylmethyl group plays an important role in the formation of 5-H thiazoles. A wide range of substituents at the 2-position of a thiazole ring tolerated the reaction conditions, and the intramolecular cyclization reaction proceeded smoothly. However, a phenyl substituent at the 4-position of a thiazole ring significantly reduced the yields of 5-H thiazoles.