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

Jones, AM and Patterson, S and Lorion, ML and 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. 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.

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