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RESEARCH ARTICLE
Contents Vol 72(4)

Friedel–Crafts Chemistry. Part 53. Divergent and Diversity-Oriented Synthesis of Condensed Indole Scaffolds via Friedel–Crafts Ring Closure Approach

Hassan A. K. Abd El-Aal A B and Ali A. Khalaf A
+ Author Affiliations
- Author Affiliations

A Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt.

B Corresponding author. Email: hassankotb33@yahoo.com

Australian Journal of Chemistry 72(4) 276-287 https://doi.org/10.1071/CH18537
Submitted: 31 October 2018  Accepted: 6 December 2018   Published: 23 January 2019

Abstract

A series of indole-fused medium-sized N-heterocyclic systems 10a–h were prepared from laboratory-synthesized indole-based esters 9a–h via intramolecular Friedel–Crafts cyclizations induced by both trifluoromethanesulfonic acid and AlCl3/CH3NO2 catalysts under suitable conditions. The synthetic sequence to precursors 9a–h that started from simple N-methylindole-2-carboxylic acid involved conversion to aminoindoles 2a, b, reaction with α,β-unsaturated acid chlorides to yield acyclic amides 5a–d, ring closure to tricyclic lactams 6a–d, and carbonyl reduction to respective pyrido and azepino tricyclic amines 7a–d, which finally underwent N-alkylations with α- or β-haloesters to produce the required ester precursors. The structures of synthesized compounds without stereochemical implications are established using both spectral and analytical data.


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