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Issue 2, 2011
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Nitrogen heteroaromatic cations by [2+2+2] cycloaddition

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Abstract

A modular approach to the construction of monocationic quaternary N-heteroaromatic frameworks was developed capitalizing on a direct pyridine-type nitrogen quaternization followed by metal-catalyzed [2+2+2] cycloaddition with gaseous acetylene. The flexibility of the route is demonstrated on 12 diverse scaffolds based on pyridinium, quinolinium, thiazolium, benzothiazolium, imidazolium, and pyrimidinium. Electrochemical study revealed a quinolinium redox system with two electrochemically distinct forms that are interconverted by a homogeneous chemical reaction triggered by fast electron transfers (reduction at −0.7 V and oxidation at −0.05 V).

Graphical abstract: Nitrogen heteroaromatic cations by [2+2+2] cycloaddition

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Publication details

The article was received on 28 Jul 2010, accepted on 20 Sep 2010 and first published on 29 Sep 2010


Article type: Paper
DOI: 10.1039/C0OB00507J
Org. Biomol. Chem., 2011,9, 450-462

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    Nitrogen heteroaromatic cations by [2+2+2] cycloaddition

    M. Čížková, V. Kolivoška, I. Císařová, D. Šaman, L. Pospíšil and F. Teplý, Org. Biomol. Chem., 2011, 9, 450
    DOI: 10.1039/C0OB00507J

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