Synthesis of Isoxazole-5-carboxylates by Cyclization of Oxime 1,4-Dianions with Diethyl Oxalate

Tuan Thanh Dang; Uwe Albrecht; Peter Langer

doi:10.1055/s-2006-942464

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Synthesis 2006(15): 2515-2522
DOI: 10.1055/s-2006-942464

PAPER

Synthesis of Isoxazole-5-carboxylates by Cyclization of Oxime 1,4-Dianions with Diethyl Oxalate

Tuan Thanh Dang^a,b, Uwe Albrecht^b, Peter Langer*^a,c
^a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: peter.langer@uni-rostock.de;
^b Institut für Biochemie, Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany
^c Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany

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Publication History

Received 7 December 2005
Publication Date:
04 July 2006 (online)

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Abstract

The cyclization of oxime dianions with diethyl oxalate afforded 4,5-dihydro-5-hydroxyisoxazole-5-carboxylates, which were transformed into isoxazole-5-carboxylates by acid-mediated dehydration. The reaction of the dilithiated oximes of cycloheptanone and cyclooctanone resulted in the formation of 1,2-oxazin-6-ones rather than isoxazoles.

Keywords

cyclizations - dianions - oxalic acid derivatives - one-pot reactions - oximes

References

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