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

Anastasiya G. Mal’kina; Olga G. Volostnykh; Anton V. Stepanov; Igor A. Ushakov; Konstantin B. Petrushenko; Boris A. Trofimov

doi:10.1055/s-0033-1340009

Synthesis, Table of Contents

Synthesis 2013; 45(24): 3435-3441
DOI: 10.1055/s-0033-1340009

paper

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

Anastasiya G. Mal’kina

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

Olga G. Volostnykh

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

Anton V. Stepanov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

Igor A. Ushakov

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

Konstantin B. Petrushenko

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

,

Boris A. Trofimov*

A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation Fax: +7(3952)419346 Email: boris_trofimov@irioch.irk.ru

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Abstract

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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

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References

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