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(±)-2-Aryl-2,3-dihydro-4(1H)-quinolinones by a tandem reduction–Michael addition reaction

✍ Scribed by Richard A. Bunce; Baskar Nammalwar

Publisher
Journal of Heterocyclic Chemistry
Year
2011
Tongue
English
Weight
128 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

An efficient synthesis of (±)‐2‐aryl‐2,3‐dihydro‐4(1__H__)‐quinolinones has been developed from chalcones prepared from 2′‐nitroacetophenone and a series of substituted benzaldehydes. The cyclization sequence is initiated by reduction of the nitro group under dissolving metal conditions using iron powder in concentrated hydrochloric acid. Milder conditions, using acetic acid or acetic acid–phosphoric acid as the reaction medium, were less satisfactory. Procedural details as well as a mechanistic discussion and reaction optimization studies are presented. J. Heterocyclic Chem., (2011).

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