A Core Switching Strategy to Pyrrolo[2,3-b]quinolines and Diazocino[1,2-a]indolinones

Jones, AM, Patterson, S, Lorion, ML, Slawin, AMZ and Westwood, NJ (2016) A Core Switching Strategy to Pyrrolo[2,3-b]quinolines and Diazocino[1,2-a]indolinones. Organic and Biomolecular Chemistry, 14 (38). pp. 8998-9011. ISSN 1477-0539

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Abstract

Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.

Item Type:	Article
Peer-reviewed:	Yes
Date Deposited:	09 Sep 2016 11:45
Publisher:	Royal Society of Chemistry
Additional Information:	This is an Author's Accepted Manuscript provided by Royal Society of Chemistry of a paper accepted for publication in Organic & Biomolecular Chemistry.
Divisions:
Subject terms:	Organic Chemistry, 0304 Medicinal And Biomolecular Chemistry, 0305 Organic Chemistry, 1115 Pharmacology And Pharmaceutical Sciences
URI:	https://e-space.mmu.ac.uk/id/eprint/617077
DOI:	https://doi.org/10.1039/C6OB01566B
ISSN	1477-0539

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