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Molecules 2009, 14(12), 4849-4857; https://doi.org/10.3390/molecules14114849

Regioselective Synthesis of New 2-(E)-Cyano(thiazolidin-2-ylidene)thiazoles

1
Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran
2
Department of Chemistry, School of Science, Islamic Azad University, Mashhad Branch, Mashhad, Iran
*
Author to whom correspondence should be addressed.
Received: 8 October 2009 / Revised: 4 November 2009 / Accepted: 25 November 2009 / Published: 25 November 2009
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Abstract

Cyclocondensation of 2-[bis(methylthio)methylene]malononitrile (1) and cysteamine (2) afforded 2-(thiazolidin-2-ylidene)malononitrile (3). This compound on treatment with NaSH gave the corresponding thioamide derivative 4a in a regioselective manner on the basis of its single crystal X-ray diffraction analysis. Reaction of this compound with several α-bromocarbonyl compounds gave new 2-(E)-cyano(thiazolidin-2-ylidene)thiazoles 5a-g.
Keywords: thiazole; thiazolidine; Hantzsch’s synthesis; heterocyclization; regioselective synthesis; X-ray crystallography thiazole; thiazolidine; Hantzsch’s synthesis; heterocyclization; regioselective synthesis; X-ray crystallography
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Bakavoli, M.; Beyzaie, H.; Rahimizadeh, M.; Eshghi, H.; Takjoo, R. Regioselective Synthesis of New 2-(E)-Cyano(thiazolidin-2-ylidene)thiazoles. Molecules 2009, 14, 4849-4857.

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