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Iodo cyclofunctionalization of 2,4-dialkenyl-1,3-dicarbonyl compounds: Synthesis of substituted 3-(2-furylidene)-2-furanones

✍ Scribed by Claudete J. Valduga; Hélio A. Stefani; Nicola Petragnani

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
73 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A facile method for the synthesis of substituted 3‐(2‐furylidene)‐2‐furanones has been developed using cyclofunctionalization reactions of 2,4‐dialkenyl‐1,3‐dicarbonyl compounds and iodine as electrophile in the presence of Na~2~CO~3~, in refluxing chloroform. Compounds 4 are obtained in modest to good yields and their structural identification was established by ^1^H NMR, ^1^H COSY, ^13^C NMR and ^1^H‐^13^C COSY. A mechanism has been proposed to rationalize the formation of the ylidene furanone.

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