Diprotodecarboxylation Reactions of 3,4-Dialkoxythiophene-2,5-dicarboxylic Acids Mediated by Ag2CO3 and Microwaves |
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Authors: | Pablo A Cisneros-Pérez Diego Martínez-Otero Erick Cuevas-Yánez |
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Institution: | Centro Conjunto de Investigación en Química Sustentable, UAEM-UNAM , Toluca , Estado de México , Mexico |
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Abstract: | An efficient and rapid method is reported to obtain 3,4-dialkoxythiophenes from 3,4-dialkoxythiophene-2,5-dicarboxylic acids through a diprotodecarboxylation reaction with Ag2CO3/AcOH as a catalytic system and microwave heating in dimethylsulfoxide (DMSO) as solvent. This methodology lets us obtain for the first time good performance with thiophenes bearing strong electron-donating groups such as alkoxides. This methodology eliminates the usage of harmful quinoline as solvent, as well as the long reaction times typically used (12–18 h) to obtain the 3,4-dialkoxythiophenes. The reaction of 7 diacids showed good yields (60–89%) following 20 min of microwave heating in a temperature range of 120–150 °C. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource(s): Full experimental and spectral details.] |
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Keywords: | Ag2CO3 3 4-dialkoxythiophene-2 5-dicarboxylic 3 4-dialkoxythiophenes microwaves protodecarboxylation |
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