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4-Thiazolidinones in Heterocyclic Synthesis: Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
Chemistry Department, Faculty of Science, Fayoum University, Fayoum 63514, A. R., Egypt
* Author to whom correspondence should be addressed.
Received: 8 May 2012; in revised form: 18 May 2012 / Accepted: 22 May 2012 / Published: 25 May 2012
Abstract: The 4-thiazolidinones 3a–d were used as a key intermediates for the synthesis of 2-arylimino-5-arylidene-4-thiazolidinones derivatives 7a–p via nucleophilic addition reactions with the arylidene malononitrile. Moreover the 4-thiazolidinones 3a and 3c condensed with the DMF-DMA to form the corresponding enamines 8 and 9 depending on the reaction conditions. Otherwise the 4-thiazolidinone 3b reacts regioselectively with DMF-DMA to afford the enaminones 10 and 11, respectively. The latter reacts with many heterocyclic amines affording polyfunctionally substituted fused pyrimidine derivatives 13–18. The enamine 8b was also reacted with the 3-amino-1,2,4-triazole to afford the acyclic product 19, which could not be further cyclized to the corresponding tricyclic system 20. Moreover the 4-thiazolidinone 3c reacted with the benzenediazonium chloride to afford the arylhydrazones 12. The X-ray single crystal technique was employed in this study for structure elucidation and Z/E potential isomerism configuration determination. The X-ray crystallographic analyses of eight products could be obtained, thus establishing with certainty the structures proposed in this work.
Keywords: 4-thiazolidinone; enaminones; arylidene malononitrile; dimethylformamide dimethylacetal; azolopyrimidine
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MDPI and ACS Style
Behbehani, H.; Ibrahim, H.M. 4-Thiazolidinones in Heterocyclic Synthesis: Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones. Molecules 2012, 17, 6362-6385.
Behbehani H, Ibrahim HM. 4-Thiazolidinones in Heterocyclic Synthesis: Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones. Molecules. 2012; 17(6):6362-6385.
Behbehani, Haider; Ibrahim, Hamada Mohamed. 2012. "4-Thiazolidinones in Heterocyclic Synthesis: Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones." Molecules 17, no. 6: 6362-6385.