Fused thia-heterocycles via isothiocyanates. Part II. A convenient synthesis of some new thieno[2,3-b]thiopyran-4-one derivatives
Author:
El-Agha Lana Z.1, El-Abadelah Mustafa M.1, Kamal Marwan R.1, Sabri Salim S.1, Al-As’ad Randa M.2, Voelter Wolfgang3
Affiliation:
1. Chemistry Department, Faculty of Science , The University of Jordan , Amman 11942 , Jordan 2. Department of Chemistry, Faculty of Science , Al-Hussein Bin Talal University , Ma’an 71111 , Jordan 3. Interfakultäres Institut für Biochemie , Universität Tübingen , Hoppe-Seyler Straße 4 , 72076 Tübingen , Germany
Abstract
Abstract
A facile synthesis of some methyl 5-(arylamino)-4-oxothieno[2,3-b]thiopyran-6-carboxylates 6a–g is achieved via direct reaction of deprotonated methyl 3-(2,5-dichlorothien-3-yl)-3-oxopropanoate with aryl isothiocyanates in anhydrous tetrahydrofuran (THF) under reflux. Upon saponification of 6a,b, the ester group is eliminated, most logically via decarboxylation of the presumably-formed carboxyl group. Structures of the new compounds 6a–g and 7a,b are supported by microanalytical and spectral [NMR, MS electron impact (EI) and HRMS] data.
Publisher
Walter de Gruyter GmbH
Subject
General Chemistry
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