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Iodo cyclofunctionalization of 2,4‐dialkenyl‐1,3‐dicarbonyl compounds: Synthesis of substituted 3‐(2‐furylidene)‐2‐furanones
Author(s) -
Valduga Claudete J.,
Stefani Hélio A.,
Petragnani Nicola
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390406
Subject(s) - chemistry , chloroform , electrophile , iodine , carbon 13 nmr , proton nmr , medicinal chemistry , organic chemistry , stereochemistry , catalysis
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.