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Paper | Special issue | Vol 54, No. 1, 2001, pp.201-208
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)17
Thionation of N-Acylthreonine and Its Methyl Ester with Lawesson's Reagent: Synthesis of 5-Oxazolones, 5-Thiazolones and Thiazolines

Mayuko Ori and Takehiko Nishio*

*Department of Chemistry, University of Tsukuba, Ten-nodai, Tsukuba-shi, Ibaraki, 305-8571, Japan


The treatment of N-acylthreonine (1) with Lawesson’s reagent [LR: 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide] afforded 5-oxazolones (2) in moderate yields, along with 5-thiazolones (3). On the other hand, N-acylthreonine methyl ester (5) reacted with LR to give 5-thiazolones (3) and 4-methoxycarbonylthiazolines (6).