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Synthesis 2001(16): 2435-2440
DOI: 10.1055/s-2001-18723
PAPER
© Georg Thieme Verlag Stuttgart · New York

Epoxy Imidates Highly Reactive Precursors of Epoxy Acylamidrazones, 3, 5-Diaminopyrazoles and 3, 4-Dihydro-2, 2’-Biquinoxalines.

Dominique Hurtauda, Michèle Baudy-Floc'ha, Patrick Gougeonb, Philippe Gallc, Philippe Le Grel*a
a Université de Rennes I, Groupe de Synthèse et Electrosynthèse Organiques, UMR CNRS 6510, France
b Université de Rennes I, Laboratoire du Solide et Inorganique Moléculaire, UMR CNRS 6511, France
c INSA, Laboratoire de Chimie Inorganique, Campus de Beaulieu F-35042 Rennes Cédex, France
Fax: +33(2)99286738; e-Mail: Philippe.Legrel@univ-rennes1.fr;
Further Information

Publication History

Received 10 September 2001
Publication Date:
05 August 2004 (online)

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Abstract

2-Cyano-2-carboximidic acid alkyl ester-oxiranes react with hydrazides and carbazates to give epoxy acylamidrazones. Some of the last ones are precursors of tetrasubstituted push-pull alkenes, which in turn can be efficiently converted into 3,5-diaminopyrazoles. Using ortho-phenylenediamine as nucleophile directly affords 3,4-dihydro-2, 2’-biquinoxalines.

Key words

oxiranes - epoxyacylamidrazones - diaminopyrazoles - biquinoxalines

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Crystallographic data (without structure factors) for the structure reported in this paper have been deposited at the Cambridge Crystallographic Data Center as supplementary publication no. CCDC - 135239. Copies of the data can be obtained free of charge on application to CCDC, 12 Union road, Cambridge CB2 1EZ, UK [Fax: (inter.) +44(1223)336033; E-mail: deposit@ccdc.cam.ac.uk].