Tricyclic phenanthrene systems: substituted phenanthro[9,10-e]-1,2,3-triazines and fused phenanthro-azolo-1,2,3-triazoles from cycloaddition—rearrangement sequences of 9,10-bisarylazophenanthrenes with 2π-dipolarophiles. Azolium 1,3-dipoles

Abstract

A range of new fused ring systems based on phenanthrene were obtained from cycloaddition–rearrangement reactions of 9,10-bisarylazophenanthrenes with alkyne and dipolarophiles. These new rings include substituted phenathro[9,10-e]-1,2,3-triazines, the tricyclic systems, substituted 3a,6a-(biphen-2,2′-yl)hexahydropyrrolo[2,3-d]-1,2,3-triazoles and substituted 3a-6a-(biphen-2,2′-yl)-hexahydroimidazo[4,5-d]-1,2,3-triazoles. X-Ray crystal structures are reported on 2-(p-bromophenyl)-4-methoxycarbonyl-4-(p-bromophenyliminomethoxalyl)-3,4-dihydrophenanthro[9,10-e]-1,2,3-triazin-2-ium-3-ide 6b, and 2,4-diphenyl-3a,6a-(biphen-2,2′-yl)-5,6-endo-dicarboxy-N-phenylimido)-1,3a,4,5,6,6a-hexahydropyrrolo[2,3-d]-1,2,3-triazol-2-ium-1-ide 11a.