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Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles

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17SL_Aitken_HarperRev.pdf (466.5Kb)
Date
18/08/2017
Author
Aitken, R Alan
Harper, Andrew David
Slawin, Alexandra Martha Zoya
Keywords
Cyclisation
Oxazoline
Benzofuran
Benzothiophenes
Indole
Schlosser’s base
Spiro heterocycle
QD Chemistry
DAS
Metadata
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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.
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
Publication
Synlett
Status
Peer reviewed
DOI
https://doi.org/10.1055/s-0036-1588503
ISSN
0936-5214
Type
Journal article
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
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
Collections
  • University of St Andrews Research
URL
https://www.thieme-connect.de/media/synlett/EFirst/supmat/sup_st-2017-b0311-l_10-1055_s-0036-1588503.pdf
URI
http://hdl.handle.net/10023/15513

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