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Azadienes are considered useful building blocks to the synthesis of six-membered heterocyclic cores, mainly through the hetero Diels-Alder reaction. Olefination reactions such as Wittig’s, Julia’s, and Peterson’s are normally employed in order to obtain this class of compounds. As part of the reactivity study of azoenaminones (1) prepared by our research group, such compounds were treated with diverse electrophiles. Herein we present our results concerning the synthesis of 1,3-azadienes through acetylation reaction of azoenaminones, performed in mild conditions and with very good yields.

Synthesis of polisubstituted 1,3-azadienes from enaminones