The Journal of Organic Chemistry

Cyclization of conjugated azines. Synthesis and thermal rearrangements of 1-oxo-3, 4-diaza-2, 4, 6, 7-octatetraenes (allenyl azines)

EE Schweizer, S Evans

Index: Schweizer,E.E.; Evans,S. Journal of Organic Chemistry, 1978 , vol. 43, p. 4328 - 4334

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Citation Number: 7

Abstract

The Wittig reaction of certain 2-(alkylidenehydrazono) propylidenephosphoranes with ketenes provides a general route to l-oxo-3, 4-diaza-2, 4, 6, 7-octatetraenes (allenyl azines). The allenyl azines undergo a facile intramolecular thermal cycloaddition reaction to yield pyrazolo [5, 1-~]-1, 4-oxazines and/or 4, 9-dihydropyrazolo [1, 5-b] isoquinolines depending on the nature of the substituents introduced via the ketene.