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

Valduga Claudete J. | Zendy; Stefani Hélio A. | Zendy; Petragnani Nicola | Zendy

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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.

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