Author:
El-Aal Hassan A. K. Abd,Khalaf Ali A.
Abstract
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.
Cited by
10 articles.
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1. Novel and facile synthesis of 1-benzazepines via copper-catalyzed oxidative C(sp3)–H/C(sp2)–H cross-coupling;Chemical Communications;2017
2. Friedel–Crafts Chemistry. Part 48. Concise Synthesis of Condensed Azaheterocyclic [1,8]naphthyridinones, Azepino-, Azocino-, and Azoninoquinoline Systems via Friedel–Crafts Ring Closures;Australian Journal of Chemistry;2017
3. Closely Related Benzylene-Linked Diamidophosphine Scaffolds and Their Zirconium and Hafnium Complexes: How Small Changes of the Ligand Result in Different Complex Stabilities and Reactivities;Organometallics;2016-06-23
4. Friedel–Crafts Chemistry. Part 46. Unprecedented Construction of Tricyclic Pyrazolo[3,4-b]quinolines, -[1,8]naphthyridines, -azepines, -azocines, -pyrido[3,2-g]azocines, and pyrazolo[3,4-b]azonines via Friedel–Crafts Ring Closures;Australian Journal of Chemistry;2016
5. Friedel-Crafts chemistry. Part 45: expedient new improved process for the synthesis of oxacarbazepine precursor 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine via Friedel-Crafts cycliacylations;Arkivoc;2015-04-27