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Communication | Regular issue | Vol 71, No. 5, 2007, pp.1053-1058
Published online, 20th March, 2007
DOI: 10.3987/COM-07-11012
Efficient 2-Amino-2-thiazolin-4-ones or 2-Iminothiazolidin-4-ones Formation from Thioureas and Maleimides under Solvent-Free Conditions

Tetsuro Shimo, Yuki Matsuda, Tetsuo Iwanaga, Teruo Shinmyozu, and Kenichi Somekawa*

*Department of Applied Chemistry, Faculty of Engineering, Kagoshima University, Korimoto 1-21-40, Kagoshima 890-0065, Japan

Abstract

A facile method for the construction of 2-thiazolin-4-one or thiazolidin-4-one structure is described. Condensation reactions of thiourea (1a) and maleimides (2) under solvent-free conditions gave 2-amino-2-thiazolin-4-ones (3) via Michael-type reaction, while similar reactions of N-substituted thioureas (1b-d) with 2 afforded 2-iminothiazolidin-4-ones (4). Since the solvent-free reactions of 1 with 2a afforded 3 in good yields, the synthetic method was found to be effective from the viewpoint of green chemistry.