title: [Diazabicyclic systems (VII). Cycloaddition reactions of benzocinnoline via ylidic intermediates].
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.
authors.affiliation: Institut de Médicine et Pharmacie, Iassy.
authors.forename: M
authors.initials: M
authors.lastname: Dorneanu
authors.forename: E
authors.initials: E
authors.lastname: Carp
authors.forename: I
authors.initials: I
authors.lastname: Zugrăvescu
mesh_terms: D000098:Acetophenones / Q000138:chemical synthesis*; D000480:Alkynes / Q000138:chemical synthesis; D000891:Anti-Infective Agents, Local / Q000138:chemical synthesis* / Q000494:pharmacology; D061565:Cycloaddition Reaction / Q000379:methods; D005021:Ethylamines / Q000138:chemical synthesis; D010616:Phenanthrenes / Q000138:chemical synthesis*; D011422:Propionates / Q000138:chemical synthesis; D015363:Quinolones / Q000138:chemical synthesis* / Q000494:pharmacology; D013055:Spectrophotometry, Infrared
chemical_list: D000098:Acetophenones; D000480:Alkynes; D000891:Anti-Infective Agents, Local; D005021:Ethylamines; D010616:Phenanthrenes; D011422:Propionates; D015363:Quinolones; C120258:benzo(c)cinnoline; C022918:acetylenedicarboxylic acid dimethyl ester; C506271:diethyl oxalopropionate; C006821:4-bromophenacyl bromide; C016162:triethylamine