C-(Methoxycarbonyl) ketene N-imidoylimine synthesis and rearrangement into methyl 4, 6-diazahepta-2, 4, 6-trienoates. Cycloaddition reactions with isocyanides: …

G Morel, E Marchand, A Foucaud

Index: Morel, Georges; Marchand, Evelyne; Foucaud, Andre Journal of Organic Chemistry, 1985 , vol. 50, # 6 p. 771 - 778

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Citation Number: 18

Abstract

The ketene N-imidoylimines 12 are shown to be transitory intermediates formed by the reaction of isocyanides with sulfides 1 or by the reaction of imino chloro sulfides with sodium salts of a-cyano esters 3. When the nitrogen atom of the imidoyl group bears a primary or secondary substituent, the ketene imines 12 are converted into diazatrienes 13 by a very fast 1, 5-migration of the hydrogen atom of the imidoyl group. Diazatrienes 13 that bear a ...