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Synthesis of Heterocyclic Compounds, XXXVIII. Five-membered Heterocycles by Cyclization of 3-Benzoyl-4-oxobutanenitriles

✍ Scribed by Ciller, J. A. ;Seoane, C. ;Soto, J. L.

Book ID: 102364484
Publisher: John Wiley and Sons
Year: 1985
Tongue: English
Weight: 367 KB
Volume: 1985
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.198519850106

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✦ Synopsis

Abstract

A synthesis of N‐benzylidene‐2‐furanamines 8 by means of cyanide addition to acylchalcones 2, followed by piperidine‐catalyzed cyclization in the presence of an aldehyde is reported. The 2‐pyrrolones 4 are formed together with the compounds 8. In the absence of an aldehyde no furan is obtained. The intermediate 2‐aryl‐3‐benzoyl‐4‐oxo‐4‐phenylbutanenitriles 3 are easily isolated. The N‐benzylidene‐2‐furanamines 9 are obtained from the oxonitriles 5.

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