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An efficient synthesis of 1,3-diarylbenzo[f]quinolines from 2-halogenated acetophenone, aromatic aldehyde, and naphthalen-2-amine catalyzed by iodine

✍ Scribed by Xiang-Shan Wang; Qing Li; Jie Zhou; Shu-Jiang Tu

Publisher: Journal of Heterocyclic Chemistry
Year: 2009
Tongue: English
Weight: 121 KB
Volume: 46
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.211

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✦ Synopsis

Abstract

magnified image The three‐component reaction of aromatic aldehyde, naphthalen‐2‐amine and 2‐halogenated acetophenone in THF catalyzed by 5 mol % iodine at reflux unexpectedly gave 1,3‐diarylbenzo[f]quinolines, with halogen losing in the formation of the products. The formation of unexpected 1,3‐diarylbenzo[f]quinolines was tentatively explained by Cram's rule to one of the steps in the mechanism. J. Heterocyclic Chem., (2009).

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