A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones
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.
Citation
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 . https://doi.org/10.1039/C6OB01566B
Publication
Organic & Biomolecular Chemistry
Status
Peer reviewed
ISSN
1477-0520Type
Journal article
Rights
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
Description
The 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).Collections
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