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RESEARCH ARTICLE
Contents Vol 72(12)

Synthesis of Tetracyclic Fused Quinolines via a Friedel–Crafts and Beckmann Ring Expansion Sequence

Hassan A. K. Abd El-Aal A B and Talaat I. El-Emary A
+ Author Affiliations
- Author Affiliations

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

B Corresponding author. Email: hassankotb@aun.edu.eg

Australian Journal of Chemistry 72(12) 945-956 https://doi.org/10.1071/CH19363
Submitted: 5 August 2019  Accepted: 12 September 2019   Published: 6 November 2019

Abstract

An efficient protocol for the construction of tetracyclic fused quinolines (pyrazole-fused azepino-, azocino-, and azonino[3,2-b]quinolinones) via consecutive Friedel–Crafts and Beckmann reactions has been developed. The key steps in the syntheses of these new molecular scaffolds involve acid-mediated cyclization of 2-(pyrazol-3-yl)quinoline based carboxylic acids 6a–c, 8, and 12 to ketones 13a–e, followed by Beckmann rearrangements of the corresponding oximes 14a–e to provide the tetracyclic-fused quinoline skeletons 15a–e. Structures of synthesised compounds without stereochemical implication were confirmed by NMR and elemental analyses.


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