Synthesis 2002(13): 1879-1884
DOI: 10.1055/s-2002-33910
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Straightforward Synthesis of Oxazino[2,3,4-ij]quinoline Derivatives from 8-Hydroxyquinolines

Axelle Arraulta, Gérald Guillaumeta, Jean-Michel Légerb, Christian Jarryb, Jean-Yves Mérour*a
a Institut de Chimie Organique et Analytique, UMR CNRS 6005, Université d’Orléans, BP 6759, 45067 Orléans Cedex 2, France
Fax: +33(2)38417281; e-Mail: jean-yves.merour@univ-orleans.fr ;
b Laboratoire de Chimie Physique et Cristallographie, EA 2962 Pharmacochimie, Université Victor Segalen Bordeaux II, 33076 Bordeaux Cedex, France
Further Information

Publication History

Received 7 May 2002
Publication Date:
09 September 2002 (online)

Abstract

A one-step synthesis of tricyclic dihydrofuro[3,2-f]quinoline or tetracyclic oxazinoquinoline derivatives from hydroxyquinolines and ethyl 2,3-dibromopropanoate is described. 3,4-Dibromobutan-2-one afforded 2-acetylfuro[3,2-h]quinoline derivatives and 2,3-dibromopropanenitrile gave only non-cyclized compounds when reacted with 8-hydroxyquinoline.

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Similarly compounds 3a and 4 afforded the analogous Z-cyano derivatives.