A new synthetic approach for the synthesis of novel 5H-dibenz[b,f]azepine, 5H-dibenz[b,f]-
azocine, 11H-benzo[f]pyrido[2,3-b]azepine and 6H-benzo[g]pyrido[2,3-c]azocine derivatives is
reported. The key step of this methodology is based on Friedel-Crafts ring closure of nitrogen
containing carboxylic acids and alkanols in the presence of AlCl3, P2O5 or PPA catalysts in
overall high yields. The starting carboxylic acids were prepared via an unequivocal synthetic
pathway by the basic hydrolysis of trimethyloxindole followed by N-arylation reactions.

A new synthetic approach for the synthesis of novel 5H-dibenz[b,f]azepine, 5H-dibenz[b,f]-
azocine, 11H-benzo[f]pyrido[2,3-b]azepine and 6H-benzo[g]pyrido[2,3-c]azocine derivatives is
reported. The key step of this methodology is based on Friedel-Crafts ring closure of nitrogen
containing carboxylic acids and alkanols in the presence of AlCl3, P2O5 or PPA catalysts in
overall high yields. The starting carboxylic acids were prepared via an unequivocal synthetic
pathway by the basic hydrolysis of trimethyloxindole followed by N-arylation reactions.

A simple and convenient procedure for the synthesis of some novel alkyl-substituted and aryl-substituted
julolidines is reported. Julolidines were smoothly synthesized in excellent isolated yields via Friedel–Crafts
intramolecular alkylations of heteroarylalkanols in the presence of both Brønsted (PPA) and Lewis
(AlCl3/CH3NO2) acid catalysts. The precursors alkanols, 1a–i, were readily prepared both by reaction of
selectively synthesized carboxylic acid esters and ketones with different Grignard reagents and also by
reduction of the synthesized ketones with LAH. A plausible carbocation mechanism is proposed to account
for the results. The structures of the compounds are established using both spectral and analytical data.

A simple and convenient procedure for the synthesis of some novel alkyl-substituted and aryl-substituted
julolidines is reported. Julolidines were smoothly synthesized in excellent isolated yields via Friedel–Crafts
intramolecular alkylations of heteroarylalkanols in the presence of both Brønsted (PPA) and Lewis
(AlCl3/CH3NO2) acid catalysts. The precursors alkanols, 1a–i, were readily prepared both by reaction of
selectively synthesized carboxylic acid esters and ketones with different Grignard reagents and also by
reduction of the synthesized ketones with LAH. A plausible carbocation mechanism is proposed to account
for the results. The structures of the compounds are established using both spectral and analytical data.

A simple and convenient procedure for the synthesis of some novel alkyl-substituted and aryl-substituted
julolidines is reported. Julolidines were smoothly synthesized in excellent isolated yields via Friedel–Crafts
intramolecular alkylations of heteroarylalkanols in the presence of both Brønsted (PPA) and Lewis
(AlCl3/CH3NO2) acid catalysts. The precursors alkanols, 1a–i, were readily prepared both by reaction of
selectively synthesized carboxylic acid esters and ketones with different Grignard reagents and also by
reduction of the synthesized ketones with LAH. A plausible carbocation mechanism is proposed to account
for the results. The structures of the compounds are established using both spectral and analytical data.