Summary.
The synthesis of the title compounds through variations of the Gewald reaction is presented. Knoevenagel condensation of methylketone derivatives with methyl cyanoacetate and subsequent treatment of the α,β-unsaturated nitriles with sulfur and amine resulted in the corresponding 2-aminothiophenes 5 or isomers 9 and 10. Reaction of methylketone derivatives bearing a leaving group at the methyl group under modified Gewald conditions selectively led to the formation of 4-substituted 2-aminothiophenes 9a and 12. The introduction of the sulfur atom occurs through nucleophilic displacement with sodium sulfide.
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Received July 5, 2000. Accepted (revised) August 23, 2000
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Buchstaller, HP., Siebert, C., Lyssy, R. et al. Synthesis of Novel 2-Aminothiophene-3-carboxylates by Variations of the Gewald Reaction. Monatshefte fuer Chemie 132, 279–293 (2001). https://doi.org/10.1007/s007060170137
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DOI: https://doi.org/10.1007/s007060170137