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Communication | Regular issue | Vol 9, No. 7, 1978, pp.831-840
Published online, 1st January, 1970
DOI: 10.3987/R-1978-07-0831
A Simple Synthesis of 4-Thiazolidinones, Tetrahydro-1,3-thiazin-4-one and Hexahydro-1,3-thiazepin-4-ones from Amide-Thiols (Studies on the Syntheses of Heterocyclic Compounds 749)

Tetsuji Kametani,* Kazuo Kigasawa, Mineharu Hiiragi, Nagatoshi Wagatsuma, Toshitaka Kohagisawa, and Hitoshi Inoue

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Acid-catalyzed cyclisation reaction of the secondary amides (3 - 10) possessing a mercapto group at α-, β- or γ-position with aldehydes gave some novel 4-thiazolidinones (11 - 14), tetrahydro-1,3-thiazin-4-ones (15 - 21), and hexahydro-1,3-thiazepin-4-ones (22 and 23), and the reduction of the cyclisation products, 12, 16 and 23 with lithium aluminium hydride afforded thiazolidine (26), tetrahydro-1,3-thiazine (27), and hexahydro-1,3-thiazepine (28), respectively.