Synthesis 2013; 45(24): 3435-3441
DOI: 10.1055/s-0033-1340009
paper
© Georg Thieme Verlag Stuttgart · New York

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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Publikationsverlauf

Received: 14. August 2013

Accepted after revision: 23. September 2013

Publikationsdatum:
23. Oktober 2013 (online)


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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.

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