New Access to Oxazolopyridines via Hydroxyamidine Derivatives; Application to Quinolines

Ethel Garnier; Stéphanie Blanchard; Ivan Rodriguez; Christian Jarry; Jean-Michel Léger; Paul Caubère; Gérald Guillaumet

doi:10.1055/s-2003-41052

PAPER

New Access to Oxazolopyridines via Hydroxyamidine Derivatives; Application to Quinolines

Ethel Garnier^a, Stéphanie Blanchard^a, Ivan Rodriguez^a, Christian Jarry^b, Jean-Michel Léger^b, Paul Caubère*^a, Gérald Guillaumet*^a
^a Institut de Chimie Organique et Analytique, UMR-CNRS 6005, Université d’Orléans, B.P. 6759, 45067 Orléans Cedex 2, France
Fax: +33(2)38417078; e-Mail: gerald.guillaumet@univ-orleans.fr;
^b Pharmacochimie, EA 2962, Université Victor Segalen Bordeaux 2, 146 rue Léo Saignat, 33076 Bordeaux cedex, France

Abstract

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Abstract

Several 2-aryl and 2-heteroaryloxazolo[4,5-b]pyridines were synthesised in high yields from zwitterion or hydroxyamidine derivatives by heating in dimethylacetamide. These intermediates were generated via hetarynic reaction with the complex base NaNH₂-t-BuONa (5:2). The same reactions were possible with quinoline derivatives.

Key words

cyclizations - heterocycles - zwitterions - pyridines - quinolines

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References

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