[Diazabicyclic systems (VII). Cycloaddition reactions of benzocinnoline via ylidic intermediates]
M Dorneanu1, E Carp, I Zugrăvescu
1Institut de Médicine et Pharmacie, Iassy.
Abstract:
By the reaction of p-bromo-phenacyl bromide on the 3,8-dimethyl- and the 3,8-di-methoxy-benzocinnoline, a cycloimmonium salts was obtained which, in the presence of triethylamine, was converted to benzocinnolinium-phenacylides. The existence in situ of the ylids was furnished evidence of the 3+2 dipolar cyclo- addition reactions with various dipolarophiles, such dimethyl and diethyl acetylenedicarboxylate, diethyl propiolate and also with diethyl azodicarboxylate. Thus, the application of the 1.3-dipolar additions is a successful route for the synthesis of some new bicyclic two nitrogen bridged systems.
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