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Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles
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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 | 250317422 | |
dc.identifier | a313cf22-92d4-4cc8-a4b3-375d9a3d647e | |
dc.identifier | 85025152051 | |
dc.identifier | 000408093400012 | |
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 | ORCID: /0000-0001-6959-5311/work/35360442 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/56861625 | |
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.format.extent | 477759 | |
dc.language.iso | eng | |
dc.relation.ispartof | Synlett | 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.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 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 |
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