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Investigation into the reaction of 2-amino-4,5-dimethylthiophene-3-carboxamide with iso(and isothio)cyanates under microwave irradiation
✍ Scribed by Abolghasem Davoodnia; Mohammad Rahimizadeh; Hoda Atapour-Mashhad; Niloofar Tavakoli-Hoseini
- Publisher
- John Wiley and Sons
- Year
- 2009
- Tongue
- English
- Weight
- 78 KB
- Volume
- 20
- Category
- Article
- ISSN
- 1042-7163
- DOI
- 10.1002/hc.20557
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✦ Synopsis
Abstract
The reaction of 2‐amino‐4,5‐dimethyl‐ thiophene‐3‐carboxamide with iso(and isothio) cyanates for the synthesis of thieno[2,3‐d]pyrimidines has been investigated. The reactions under microwave irradiation in the presence of N,N‐dimethyl acetamide as solvent gave 5,6‐dimethylthieno[2,3‐d]pyrimidine‐2,4(1__H__,3__H__)‐dione, 5,6‐dimethyl‐2‐thioxo‐2,3‐dihy‐ drothieno[2,3‐d]pyrimidin‐4(1__H__)‐one, and 2‐aryla‐ mino‐5,6‐dimethylthieno[2,3‐d]pyrimidin‐4(3__H__)‐one derivatives. These reactions probably proceed through intermediates 4,5‐dimethyl‐2‐substitutedcarbamoth‐ ioylaminothiophene‐3‐carboxamides. Two of these intermediates were isolated. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:346–349, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20557
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