One-Pot Stereoselective Synthesis of Alkyl (Z)-2-[4-Oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetates from Acetylenic Esters and N, N' -Diphenylthiourea

Author: Gonbari Monireh Heshmati   Ramazani Ali   Souldozi Ali  

Publisher: Taylor & Francis Ltd

ISSN: 1042-6507

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Vol.184, Iss.2, 2009-02, pp. : 309-314

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Abstract

N, N' -diphenylthiourea reacts with dialkyl acetylenedicarboxylates in acetone to form 1:1 adducts, which undergo a cyclization reaction to produce alkyl (Z)-2-[4-oxo-3-phenyl-2-(phenylimino)-1,3-thiazolan-5-yliden]acetates in fairly good yields. NMR spectra indicated that the reaction is completely stereoselective.

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