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E-Journal of Chemistry
Volume 9, Issue 3, Pages 1518-1525
http://dx.doi.org/10.1155/2012/896454

Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives

Department of Chemistry, Faculty of Sciences Ilam Branch, Islamic Azad University, Ilam, Iran

Received 26 September 2011; Accepted 13 November 2011

Copyright © 2012 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR, 1H NMR and 13C NMR data.