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Issue 8, 2018
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Divergent access to N-hydroxypyrroles and isoxazoles via the gold(I)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes

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Abstract

The divergent regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes by a suitable choice of a gold(I) or a Brønsted acid catalyst, leading to 4-trifluoromethyl-N-hydroxypyrroles or 4-trifluoromethyl-5-alkylisoxazoles was developed. In order to avoid the tedious separation of unstable N-(2-trifluoromethyl-3-alkynyl) oximes, an easy two-step, one-pot synthesis of 4-trifluoromethyl-5-alkylisoxazoles was realized via the sequential oxidation of the corresponding hydroxylamines and subsequent treatment with the reductant, sodium thiosulfate (Na2S2O3). This two-step, one-pot procedure is a complementary method for the synthesis of 4-trifluoromethyl-5-alkylisoxazole from those unstable N-(2-trifluoromethyl-3-alkynyl) oximes.

Graphical abstract: Divergent access to N-hydroxypyrroles and isoxazoles via the gold(i)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes

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Publication details

The article was received on 15 Dec 2017, accepted on 29 Jan 2018 and first published on 29 Jan 2018


Article type: Paper
DOI: 10.1039/C7OB03107F
Citation: Org. Biomol. Chem., 2018,16, 1375-1380
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    Divergent access to N-hydroxypyrroles and isoxazoles via the gold(I)- or Brønsted acid-catalysed regioselective cyclization of N-(2-trifluoromethyl-3-alkynyl) oximes

    Q. Zeng, L. Zhang, Y. Xiao and J. Zhang, Org. Biomol. Chem., 2018, 16, 1375
    DOI: 10.1039/C7OB03107F

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