Modern Friedel-Crafts chemistry. Part 35. New synthetic approach to substituted indolo[2,1-a][2]benzazepines and indolo[2,1-a]isoquinolines via Friedel-Crafts cyclialkylations

Abstract

Facile procedures for the construction of fused indole-containing heteropolycycles 1a-f and 2a-c have been developed. The methodology involves Friedel-Crafts cyclialkylations of heteoraryl alkanols in the presence of both Brönsted (PPA) and Lewis (AlCl 3 /CH 3 NO 2 ) acid catalysts. The starting alkanols 6a-f and 12a-c were smoothly obtained both by reactions of the corresponding carboxylic acid esters and the corresponding ketones with Grignard reagents. Overall, this approach allows for easy and efficient access to polycyclic indoles from easily synthesized precursors.

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

“…[36][37][38][39][40][41] In our previous work 41 we developed a synthetic methodology for the construction of nine substituted 5,6- H NMR data allowed an unambiguous statement of the formation of the heterocyclic alkanols. Thus, the 1 H NMR spectrum for alcohol 9a displayed five signals in which aromatic protons appeared at δ 6.45-7.7.…”