Files in this item
Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles
Item metadata
dc.contributor.author | Aitken, R Alan | |
dc.contributor.author | Harper, Andrew David | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.date.accessioned | 2018-07-17T23:34:41Z | |
dc.date.available | 2018-07-17T23:34:41Z | |
dc.date.issued | 2017-08-18 | |
dc.identifier.citation | Aitken , R A , Harper , A D & Slawin , A M Z 2017 , ' Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles ' , Synlett , vol. 28 , no. 14 , pp. 1738-1742 . https://doi.org/10.1055/s-0036-1588503 | en |
dc.identifier.issn | 0936-5214 | |
dc.identifier.other | PURE: 250317422 | |
dc.identifier.other | PURE UUID: a313cf22-92d4-4cc8-a4b3-375d9a3d647e | |
dc.identifier.other | Scopus: 85025152051 | |
dc.identifier.other | ORCID: /0000-0001-6959-5311/work/35360442 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861625 | |
dc.identifier.other | WOS: 000408093400012 | |
dc.identifier.uri | https://hdl.handle.net/10023/15513 | |
dc.description | The authors thank EPSRC (UK) for a DTA studentship (Grant No. EP/L505079/1) and the EPSRC UK National Mass Spectrometry Facility at Swansea University | en |
dc.description.abstract | Treatment of ortho-benzyloxyphenyloxazolines with butyllithium and potassium t-butoxide results in cyclisation with ring-opening of the oxazoline to give 2-aryl-3-aminobenzofurans. The reaction also occurs with the corresponding benzylthio- and benzylamino-compounds to give benzothiophenes and indoles, respectively. Use of an ortho-allyloxyphenyloxazoline gives the corresponding 2-vinylbenzofuran, while both α-methylbenzyloxy and benzylsulfonyl compounds form stable spirooxazolidine products. The X-ray structure of an aminobenzothiophene product has been determined. | |
dc.format.extent | 5 | |
dc.language.iso | eng | |
dc.relation.ispartof | Synlett | en |
dc.rights | © 2017 Georg Thieme Verlag Stuttgart · New York. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1055/s-0036-1588503 | en |
dc.subject | Cyclisation | en |
dc.subject | Oxazoline | en |
dc.subject | Benzofuran | en |
dc.subject | Benzothiophenes | en |
dc.subject | Indole | en |
dc.subject | Schlosser’s base | en |
dc.subject | Spiro heterocycle | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles | 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.identifier.doi | https://doi.org/10.1055/s-0036-1588503 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2018-07-18 | |
dc.identifier.url | https://www.thieme-connect.de/media/synlett/EFirst/supmat/sup_st-2017-b0311-l_10-1055_s-0036-1588503.pdf | en |
This item appears in the following Collection(s)
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.