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Paper | Regular issue | Vol 55, No. 7, 2001, pp.1283-1289
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9227
A Simple Construction of 2-Phenylimino-1,3-thiazolidin-4-ones

Hoh-Gyu Hahn,* Kee Dal Nam, and Heduck Mah

*Organic Chemistry Laboratory, Korea Institute of Science and Technology, P.O. Box 131, Cheongryang, Seoul 136-791, Korea

Abstract

A new methodology for the construction of 2-phenylimino-1,3-thiazolidin-4-one skeleton is described. Reaction of maleic anhydride (5a) or maleimides (5b, 5c) with thiourea (6) gave the corresponding 2-imino-1,3-thiazolidin-4-ones (7) and (9) respectively. The reaction proceeded with high yield in polar solvents. In non-polar solvents at high temperature, however, isothiocyanate (8) was formed as a by-product presumably by the pyrolysis of thiourea (6). The proposed mechanism of the reaction was discussed.