1446358-27-5Relevant articles and documents
Friedel-crafts chemistry. Part 39. unprecedented facile route to the synthesis of benzo[b][1]benzazepines via intramolecular friedel-crafts cyclialkylations
El-Aal, Hassan A. K. Abd,Khalaf, Ali A.
, p. 635 - 645 (2013/07/26)
A series of six pharmaceutically promising 5,6-dihydro-11H-benzo[b][1] benzazepine derivatives (1c-h) were cleanly prepared by Friedel-Crafts cyclialkylations of nitrogen-containing alkanols in the presence of AlCl3, 85% H2SO4 or polyphosphoric acid catalysts. The precursor alkanols (13a-f) were readily prepared by reaction of two synthesized carboxylic acid esters (12a, b) with different Grignard reagents. Also, two dibenzo[b,f]azepinones (15a, b) were prepared by Friedel-Crafts cycliacylation and reduced to the corresponding 5,6-dihydro-11H-benzo[b][1]benzazepines (1a, b). Overall, this approach allows easy and efficient access to polytricyclic amines from easily synthesized alkanols or cycloketones. A plausible carbocation mechanism is proposed to account for the results.