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

Jones, Alan M.; Patterson, Stephen; Lorion, Magali Myriam; Slawin, Alexandra Martha Zoya; Westwood, Nicholas James

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dc.contributor.author	Jones, Alan M.
dc.contributor.author	Patterson, Stephen
dc.contributor.author	Lorion, Magali Myriam
dc.contributor.author	Slawin, Alexandra Martha Zoya
dc.contributor.author	Westwood, Nicholas James
dc.date.accessioned	2017-08-29T23:32:02Z
dc.date.available	2017-08-29T23:32:02Z
dc.date.issued	2016-10-14
dc.identifier.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	en
dc.identifier.issn	1477-0520
dc.identifier.other	PURE: 245405321
dc.identifier.other	PURE UUID: d6096037-1077-49c8-bb7a-8a95bfae2116
dc.identifier.other	Scopus: 84989271279
dc.identifier.other	ORCID: /0000-0003-0630-0138/work/56424125
dc.identifier.other	ORCID: /0000-0002-9527-6418/work/56861337
dc.identifier.other	WOS: 000385173200014
dc.identifier.uri	http://hdl.handle.net/10023/11562
dc.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).	en
dc.description.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.
dc.format.extent	14
dc.language.iso	eng
dc.relation.ispartof	Organic & Biomolecular Chemistry	en
dc.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	en
dc.subject	Rearrangement	en
dc.subject	Medium-sized ring	en
dc.subject	Core-switching	en
dc.subject	Diversity-Oriented Synthesis	en
dc.subject	Pyrrolo[2,3-b]quinoline	en
dc.subject	Diazocino[1,2-a]indolinone	en
dc.subject	QD Chemistry	en
dc.subject	DAS	en
dc.subject.lcc	QD	en
dc.title	A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones	en
dc.type	Journal article	en
dc.description.version	Postprint	en
dc.contributor.institution	University of St Andrews. School of Chemistry	en
dc.contributor.institution	University of St Andrews. EaSTCHEM	en
dc.contributor.institution	University of St Andrews. Biomedical Sciences Research Complex	en
dc.identifier.doi	https://doi.org/10.1039/C6OB01566B
dc.description.status	Peer reviewed	en
dc.date.embargoedUntil	2017-08-29
dc.identifier.url	http://www.rsc.org/suppdata/c6/ob/c6ob01566b/c6ob01566b1.pdf	en

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