A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Stephen Patterson; Magali M Lorion; Alexandra M Z Slawin; Nicholas J Westwood; Alan Jones

doi:10.1039/c6ob01566b

A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Stephen Patterson, Magali M Lorion, Alexandra M Z Slawin, Nicholas J Westwood, Alan Jones

Pharmacy

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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.

Original language	English
Pages (from-to)	8998-9011
Journal	Organic and Biomolecular Chemistry
Volume	14
Issue number	38
Early online date	30 Aug 2016
DOIs	https://doi.org/10.1039/c6ob01566b
Publication status	Published - 14 Oct 2016

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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.",

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AU - Westwood, Nicholas J

AU - Jones, Alan

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AB - 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.

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A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones

Abstract

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