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Issue 5, 2018
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Synthesis of 2-aminopyridines via ruthenium-catalyzed [2+2+2] cycloaddition of 1,6- and 1,7-diynes with cyanamides: scope and limitations

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Abstract

A practical and mild process to access 2-aminopyridine derivatives using ruthenium-catalyzed [2+2+2] cycloaddition of various 1,6- and 1,7-diynes with cyanamides is described. This straightforward atom-economical catalytic cycloaddition is scalable and showed excellent regioselectivities to approach a wide range of 2-aminopyridines of high synthetic utility. Postfunctionalization reactions of halo-containing adducts, via Pd- and Cu-catalyzed cross-couplings as well as cyanation and amination reactions, delivered substituted 2-aminopyridine derivatives in good to excellent yields.

Graphical abstract: Synthesis of 2-aminopyridines via ruthenium-catalyzed [2+2+2] cycloaddition of 1,6- and 1,7-diynes with cyanamides: scope and limitations

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Publication details

The article was received on 12 Dec 2017, accepted on 24 Jan 2018 and first published on 01 Feb 2018


Article type: Paper
DOI: 10.1039/C7NJ04933A
Citation: New J. Chem., 2018,42, 3222-3235
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    Synthesis of 2-aminopyridines via ruthenium-catalyzed [2+2+2] cycloaddition of 1,6- and 1,7-diynes with cyanamides: scope and limitations

    F. Ye, F. Boukattaya, M. Haddad, V. Ratovelomanana-Vidal and V. Michelet, New J. Chem., 2018, 42, 3222
    DOI: 10.1039/C7NJ04933A

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