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

Axelle  Arrault; Gérald  Guillaumet; Jean-Michel  Léger; Christian  Jarry; Jean-Yves  Mérour

doi:10.1055/s-2002-33910

PAPER

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

Axelle Arrault^a, Gérald Guillaumet^a, Jean-Michel Léger^b, Christian Jarry^b, 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

Abstract

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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.

Key words

hydroxyquinolines - oxazino[2,3,4-ij]quinolines - ethyl dihydrofuro[3,2-h]quinoline-2-carboxylate - cyclization

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References

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