Synthesis 2018; 50(24): 4905-4914
DOI: 10.1055/s-0037-1609916
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Functionalized 5-Amino-3(2H)-furanones via Base-Catalyzed Ring-Cleavage/Recyclization of 4-Cyano-3(2H)-furanones in the Presence of Water

Olga G. Volostnykh
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: shemyakina@irioch.irk.ru
,
Olesya A. Shemyakina*
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: shemyakina@irioch.irk.ru
,
Anton V. Stepanov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: shemyakina@irioch.irk.ru
,
Igor A. Ushakov
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: shemyakina@irioch.irk.ru
,
Tatyana N. Borodina
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russian Federation   Email: shemyakina@irioch.irk.ru
› Author Affiliations
Further Information

Publication History

Received: 08 June 2018

Accepted after revision: 19 July 2018

Publication Date:
15 August 2018 (online)


Abstract

5-Alkyl/aryl/hetaryl-4-cyano-3(2H)-furanones undergo ring-cleavage/recyclization in the presence of water under mild conditions [MOH (M = Na, K), aqueous ethanol, 20–25 °C] to afford 4-acyl/aroyl/hetaroyl-5-amino-3(2Н)-furanones in 75–99% yields.

Supporting Information