A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones
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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.
Jones , A M , Patterson , S , Lorion , M M , Slawin , A M Z & Westwood , N J 2016 , ' A core switching strategy to pyrrolo[2,3- b ]quinolines and diazocino[1,2- a ]indolinones ' Organic & Biomolecular Chemistry , vol 14 , no. 38 , pp. 8998-9011 . DOI: 10.1039/C6OB01566B
Organic & Biomolecular Chemistry
Copyright 2016 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1039/C6OB01566B
DescriptionThe authors gratefully acknowledge the Royal Society (NJW held a URF at the time this work was done), and the BBSRC for PhD funding through the Doctoral Training Scheme (AMJ).
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