(20.1.86) Z-Aza-l,3-dienes. A New Approach to Substituted 2-AminopyrazinesTreatment of enamines by tosylated isonitrosomalono derivatives gives access to 5-dialkylamino-1,l-dicyano 2-aza-l,3-dienes (or I -methoxycarbonyl analogous) which are precursors of various regiospecific 5,6-substituted 2-amino-3-cyano (or methoxycarbonyl) pyrazines. Some examples of utilisation of these intermediates for synthesis of lumarines, pteridines, and other bicyclic skeletons are described.Nous avons prectdemment decrit [ 11 un procede original conduisant dans des conditions douces a la formation d'une liaison C-N si l'on oppose des derives isonitrosomaloniques tosyles 1 a des enamines (SchPma 1). Les azadiPnes 2 ainsi formb sont des solides cristallises dont les proprietks spectroscopiques (absorption UVjVIS dans la region de 450 nm, rotation restreinte pour le groupe R,N, proton vinylique sur C(4) aux environs de 7,5 ppm, v(C=N) < 2200 cm-') indiquent un caractkre tr2s polaire analogue a celui d'une merocyanine. Cette polarite se traduit par une deprotonation aisee d'un mbthylene fix6 sur C(4), propriett qui nous a permis d'isomeriser certains de ces azadihes en ylures d'azomkthines stables [2]. L'attaque nucleophile sur C(4) est une autre consequence de cette polarite.
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