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Paper | Regular issue | Vol 89, No. 5, 2014, pp.1183-1194
Published online, 25th March, 2014
DOI: 10.3987/COM-14-12967
■ Ring Transformation of the S-(2-Oxo-2,3-dihydro-1-benzofuran-3-yl)isothiuronium Bromides to 5-(2-Hydroxyphenyl)-2-imino-1,3-thiazolidin-4-ones

Richard Kammel and Jiří Hanusek*

*Institute of Organic Chemistry and Technology, University of Pardubice, Studentská 573, Pardubice, 532 10, Czech Republic

Abstract

Synthesis of thirteen substituted 5-(2-hydroxyethyl)-2-phenylimino-1,3-thiazolidin-4-ones is described starting from easily available and stable S-(2-oxo-2,3-dihydro-1-benzofuran-3-yl)isothiuronium bromides. The transformation proceeds under mild conditions, is very simple to perform, and is applicable to a wide range of substituents on isothiuronium moiety. Some 1,3-thiazolidin-4-ones show dynamic NMR behavior in solution because of prototropy tautomerism and E-/Z-stereoisomerism. Thermochromic behavior was observed for all synthesized compound.