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Issue 27, 2013
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Electrophilic α-cyanation of 1,3-dicarbonyl compounds

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Abstract

Electrophilic α-cyanation of activated methylene compounds was achieved under mild basic conditions using commercially available TsCN as a CN+ equivalent. A series of 1,3-dicarbonyl compounds, both cyclic and acyclic, were found to be suitable substrates for this transformation. Subjecting 1,1,1-trifluoro-1,3-dicarbonyl compounds to a modified procedure resulted in the formation of α-cyano ketones after trifluoroacetyl group fragmentation. An efficient one-pot cyanation/pyrazole formation sequence to 4-cyano pyrazoles from 1,3-diketones has also been developed.

Graphical abstract: Electrophilic α-cyanation of 1,3-dicarbonyl compounds

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Publication details

The article was received on 20 Mar 2013, accepted on 18 Apr 2013 and first published on 19 Apr 2013


Article type: Paper
DOI: 10.1039/C3RA41376D
RSC Adv., 2013,3, 10731-10735

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    Electrophilic α-cyanation of 1,3-dicarbonyl compounds

    R. Akula, Y. Xiong and H. Ibrahim, RSC Adv., 2013, 3, 10731
    DOI: 10.1039/C3RA41376D

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