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Reactivity of Esters and Nitriles of 2-(3-Acylthioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic Acids 1. Acid-Catalyzed Cyclization and Desulfanation Reaction in the Presence of Secondary Amines

P. Pazdera and I. Preissov√°

Department of Organic Chemistry, Faculty of Natural Sciences, Masaryk University, CS-611 37 Brno

 

Abstract: Esters and nitriles of 2-(3-acylthioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acids were cyclized in a solution of concentrated sulfuric acid at room temperature to substituted thieno[2,3-d]-[1,3]-thiazines. Further they were treated with mercuric oxide (desulfanation reaction) in the presence of secondary amines (diethylamine, morpholine, piperidine) forming corresponding 1-acylguanidines in some cases accompanied by the cyclization to thieno[2,3-d]-pyrimidines. These were also prepared by the cyclization of 1-acylguanidines in concentrated sulfuric acid at room temperature.

Full paper in Portable Document Format: 466a396.pdf

 

Chemical Papers 46 (6) 396–405 (1992)

Wednesday, August 10, 2022

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