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

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

References

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  Cheguillaume, A.; Salaün, A.; Sinbandhit , S.; Potel, M.; Gall, P.; Baudy-Floc’h, M.; Le Grel, P. J. Org. Chem. 2001, in press.

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11

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.) [phone]; E-mail: [e-mail]].