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Synthesis 2002(8): 1037-1042
DOI: 10.1055/s-2002-31953
PAPER
© Georg Thieme Verlag Stuttgart · New York

Regiospecific Synthesis of 3-Alkyl-2-aryl-4-trifluoromethylbenzo[h]quinolines by Intramolecular Cyclization of N-(2-Alkyl-1-aryl-3-oxo-4,4,4-trifluorobut-1-en-1-yl)-1-naphthylamines

Helio Gauze Bonacorso*, Simone Helena Goulart Duarte, Nilo Zanatta, Marcos Antonio Pinto Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900 - Santa Maria, RS - Brazil
Fax: +55(55)2208031; e-Mail: heliogb@base.ufsm.br;
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Publication History

Received 24 November 2001
Publication Date:
03 June 2002 (online)

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Abstract

A convenient method to obtain a series of 3-alkyl-2-aryl-4-trifluoromethylbenzo[h]quinolines derivatives 3a-l, where alkyl = H, Me; aryl = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-OMeC6H4 and 4-NO2C6H4, by intramolecular cyclization of the readily available intermediates N-(2-alkyl-1-aryl-3-oxo-4,4,4-trifluorobut-1-en-1-yl)-1-naphthylamines 2a-l using polyphosphoric acid, is reported. Compounds 2 are obtained from the reaction of 3-alkyl-4-aryl-1,1,1-trifluoro-4-alkoxybut-3-en-2-ones la-l with 1-naphthylamine under reflux in chloroform.

Key words

benzoquinolines - quinolines - enones - naphthylamines - intramolecular cyclizations