Synthesis of 5-Thienylfuran-3(2H)-ones via the Microwave-Assisted Tandem Reaction of Cyanopropargylic Alcohols with Thiophene-2-carboxylic Acids

Abstract

Tertiary cyanopropargylic alcohols undergo tandem reaction with thiophene-2-carboxylic and benzo[b]thiophene-2-carboxylic acids under microwave irradiation (MeCN, Et₃N, 100 °C, 2.5–16 h) to afford 4-cyano-5-thienylfuran-3(2Н)-ones in 69–89%. The cyano function of the synthesized furanones is readily hydrolyzed (aq EtOH, KOH, 20–25 °C, 24 h) to give quantitatively the corresponding amides, 5,5-dialkyl-4-oxo-2-(2-thienyl)-4,5-dihydrofuran-3-carboxamides.

Key words

tertiary cyanopropargylic alcohols - thiophene acids - tandem reaction - cyclization - furan-3(2H)-ones - amides

• References

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