Friedel-Crafts chemistry. Part 40. An expedient novel synthesis of some dibenz-azepines, -azocines, 11H-benzo[f]pyrido[2,3-b]azepines and 6H-benzo[g]pyrido[2,3-c]azocines

Abstract

A new synthetic approach for the synthesis of novel 5H-dibenz [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 AlCl 3 , P 2 O 5 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.

Friedel–Crafts Chemistry. Part 43. A Convergent Construction of Some New Bridged Aza-Bicyclic Analogues of Azocine, Azonine, and Azecine via Friedel–Crafts Ring Closures

“…That inspired us to start a systematic study based on our long experience in Friedel-Crafts reactions to develop ringclosure strategies for the construction of bridged and nonbridged medium-sized heteropolycycles. In our previous work, [40][41][42][43] we introduced novel methods for the construction of nine substituted 10,11-dihydro-5H-dibenz [b,f]azepines (iminodibenzyls), 5,6,11,12-tetrahydro-5H-dibenz[b,f]azocines, 5,6-dihydro-11H-benzo [f]pyrido [2,3-b]azepines, and 5,6,11,12tetrahydro-6H-benzo [g]pyrido [2,3-c]azocines via Friedel-Crafts ring closures of nitrogen-containing alcohols and carboxylic acids.…”