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Regioselective Synthesis of New 2-(E)-Cyano(thiazolidin-2-ylidene)thiazoles
Department of Chemistry, School of Sciences, Ferdowsi University of Mashhad, 91775-1436 Mashhad, Iran
Department of Chemistry, School of Science, Islamic Azad University, Mashhad Branch, Mashhad, Iran
* Author to whom correspondence should be addressed.
Received: 8 October 2009; in revised form: 4 November 2009 / Accepted: 25 November 2009 / Published: 25 November 2009
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
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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.
Bakavoli M, Beyzaie H, Rahimizadeh M, Eshghi H, Takjoo R. Regioselective Synthesis of New 2-(E)-Cyano(thiazolidin-2-ylidene)thiazoles. Molecules. 2009; 14(12):4849-4857.
Bakavoli, Mehdi; Beyzaie, Hamid; Rahimizadeh, Mohammad; Eshghi, Hossein; Takjoo, Reza. 2009. "Regioselective Synthesis of New 2-(E)-Cyano(thiazolidin-2-ylidene)thiazoles." Molecules 14, no. 12: 4849-4857.