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

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dc.contributor.authorJones, Alan M.
dc.contributor.authorPatterson, Stephen
dc.contributor.authorLorion, Magali Myriam
dc.contributor.authorSlawin, Alexandra Martha Zoya
dc.contributor.authorWestwood, Nicholas James
dc.date.accessioned2017-08-29T23:32:02Z
dc.date.available2017-08-29T23:32:02Z
dc.date.issued2016-10-14
dc.identifier245405321
dc.identifierd6096037-1077-49c8-bb7a-8a95bfae2116
dc.identifier84989271279
dc.identifier000385173200014
dc.identifier.citationJones , 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/C6OB01566Ben
dc.identifier.issn1477-0520
dc.identifier.otherORCID: /0000-0003-0630-0138/work/56424125
dc.identifier.otherORCID: /0000-0002-9527-6418/work/56861337
dc.identifier.urihttps://hdl.handle.net/10023/11562
dc.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).en
dc.description.abstractTwo 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.extent14
dc.format.extent1008502
dc.language.isoeng
dc.relation.ispartofOrganic & Biomolecular Chemistryen
dc.subjectRearrangementen
dc.subjectMedium-sized ringen
dc.subjectCore-switchingen
dc.subjectDiversity-Oriented Synthesisen
dc.subjectPyrrolo[2,3-b]quinolineen
dc.subjectDiazocino[1,2-a]indolinoneen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleA core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinonesen
dc.typeJournal articleen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.contributor.institutionUniversity of St Andrews. EaSTCHEMen
dc.contributor.institutionUniversity of St Andrews. Biomedical Sciences Research Complexen
dc.identifier.doi10.1039/C6OB01566B
dc.description.statusPeer revieweden
dc.date.embargoedUntil2017-08-29
dc.identifier.urlhttp://www.rsc.org/suppdata/c6/ob/c6ob01566b/c6ob01566b1.pdfen


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