Microwave Induced Stereoselective Synthesis of Alkyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H)-yliden)acetates from Thiourea and Dialkyl Acetylenedicarboxylates in Solvent-less Conditions
Corresponding Author(s) : Ali Ramazani
a-ramazani@mail.znu.ac.ir; aliramazani@yahoo.com
Asian Journal of Chemistry,
Vol. 17 No. 4 (2005): Vol 17 Issue 4
Abstract
Thiourea reacts with dialkyl acetylenedicarboxylates in solvent-less conditions to form 1 : 1 adducts, which undergo a cyclization reaction to produce alkyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H)-yliden)acetates under microwave irradiation and also under thermal conditions in solvent-less system in fairly good yields. Stereochemistry of the ethyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H)-yliden)acetate was established with using of X-ray single crystal structure analysis. The reaction is completely stereoselective.
Keywords
Microwave irradiation
Thiourea
Acetylenic ester
Michael addition
X-ray single crystal structure analysis
Stereoselectivity
1,3-thiazol
Ramazani, A., Reza Kazemizadeh, A., Ganjeie, B., & Ahmadi, E. (2016). Microwave Induced Stereoselective Synthesis of Alkyl Z-2-(2-amino-4-oxo-1,3-thiazol-5(4H)-yliden)acetates from Thiourea and Dialkyl Acetylenedicarboxylates in Solvent-less Conditions. Asian Journal of Chemistry, 17(4), 2375–2378. Retrieved from https://asianpubs.org/index.php/ajchem/article/view/13904
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