Base-induced cyclisation of ortho-substituted 2-phenyloxazolines to give 3-aminobenzofurans and related heterocycles
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
ISSN
0936-5214Type
Journal article
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 UniversityCollections
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