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Beilstein J Org Chem. 2012;8:1849-57. doi: 10.3762/bjoc.8.213. Epub 2012 Oct 30.

An efficient access to the synthesis of novel 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives.

Author information

  • 1Institute of Superfine Chemicals, Bohai University, Jinzhou 121000, China.

Abstract

An efficient access to the tetracyclic-fused quinoline systems, 12-phenylbenzo[6,7]oxepino[3,4-b]quinolin-13(6H)-one derivatives 4a-l, is described, involving the intramolecular Friedel-Crafts acylation reaction of 2-(phenoxymethyl)-4-phenylquinoline-3-carboxylic acid derivatives 3a-l aided by the treatment with PPA (polyphosphoric acid) or Eaton's reagent. The required starting compound (2) was obtained by Friedländer reaction of 2-aminobenzophenone (1) with 4-chloroethylacetoacetate by using CAN (cerium ammonium nitrate, 10 mol %) as catalyst at room temperature. The substrates 3a-l were prepared through one-pot reaction of ethyl 2-(chloromethyl)-4-phenylquinoline-3-carboxylate (2) and substituted phenols. Our developed strategy, involving a three-step route, offers easy access to tetracyclic-fused quinoline systems in short reaction times, and the products are obtained in moderate to good yields.

KEYWORDS:

Eaton’s reagent; Friedel–Crafts acylation; Friedländer reaction; PPA; one-pot; quinoline; tetracyclic-fused

PMID:
23209522
[PubMed]
PMCID:
PMC3511022
Free PMC Article
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