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Chemo- and regioselective reactions of 5-bromo enones/enaminones with pyrazoles

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Abstract

Reaction of 5-bromo enones with pyrazoles provided a series of unexpected N,O-aminal derivatives, through a 1,4-conjugated addition at the β-carbon of the 5-bromo enones instead of the expected nucleophilic substitution of the bromine. This reaction also furnished the 1,3-regioisomer of the pyrazole. A similar reaction of pyrazoles using 5-bromo enaminones furnished only N-alkylated pyrazoles—with high regioselectivity and at good yields—through nucleophilic substitution of the bromine.

Graphical abstract: Chemo- and regioselective reactions of 5-bromo enones/enaminones with pyrazoles

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Publication details

The article was received on 10 Jan 2019, accepted on 31 Jan 2019 and first published on 31 Jan 2019


Article type: Paper
DOI: 10.1039/C9OB00234K
Citation: Org. Biomol. Chem., 2019, Advance Article

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    Chemo- and regioselective reactions of 5-bromo enones/enaminones with pyrazoles

    P. A. Moraes, M. M. Lobo, M. A. Marangoni, A. R. Meyer, C. P. Frizzo, H. G. Bonacorso, M. A. P. Martins and N. Zanatta, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00234K

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