Reduction of quaternary salts of 3-azafluorene and 3-azafluorenone and their conversion to indenoindolizines

The tetrahydro and hexahydro derivatives with respect to the nitrogen-containing ring were obtained by reduction of 3-azafluorene and 3-azafluorenone methiodides, respectively, with sodium borohydride. Indenoindolizines with linear and angular structures were synthesized from the N-phenacyl quaternary salts of 3-azafluorenones via 1,3-dipolar cycloaddition and by the Chichibabin method. 7-Nitro-3-azafluorenone and 3-azafluorenone N-oxide were obtained. © 1983 Plenum Publishing Corporation.