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

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    0363295 - ÚOCHB 2012 RIV GB eng J - Journal Article
    Čížková, Martina - Kolivoška, Viliam - Císařová, I. - Šaman, David - Pospíšil, Lubomír - Teplý, Filip
    Nitrogen heteroaromatic cations by [2+2+2] cycloaddition.
    Organic & Biomolecular Chemistry. Roč. 9, č. 2 (2011), s. 450-462. ISSN 1477-0520. E-ISSN 1477-0539
    R&D Projects: GA ČR GA203/09/1614; GA ČR GA203/09/0705; GA MŠMT OC 140
    Institutional research plan: CEZ:AV0Z40550506; CEZ:AV0Z40400503
    Keywords : modular synthesis * N-heteroaromatic cation * [2+2+2] cycloaddition
    Subject RIV: CC - Organic Chemistry
    Impact factor: 3.696, year: 2011

    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).
    Permanent Link: http://hdl.handle.net/11104/0199276

     
     
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