O. V. Ershov, V. N. Maksimova, M. Y. Ievlev
Dec 24, 2015
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Influential Citations
7
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Journal
Russian Journal of Organic Chemistry
Abstract
2-Halopyridine and its derivatives are convenient initial compounds for the synthesis of functional pyridine derivatives through reactions of nucleophilic substitution SNAr [1–3]. Some of forming compounds possess practically important properties, in particular, 2-hydroxypyridines (tautomers of pyridin-2-ones) are characterized by intense fluorescence [4, 5], and 2-alkoxypyridines exhibit antiphlogistic activity of a wide range of action [6]. We explored the reactions of 2-chloropyridne-3,4dicarbonitriles 1а–1с [7–9] with sodium methoxide. Initial compounds 1а–1с contain two cyano groups which considerably facilitate the nucleophilic substitution of halogen but also can suffer transformation under the action of nucleophiles [10]. The presence in the structure of pyridines 1а–1с of several competing sites for the attack of О-nucleophiles requires a development of special conditions for carrying out desired transformations. The reactions in the anhydrous methanol afford exclusively 2-methoxy derivatives 2а–2с in 68‒79% yields (Scheme 1). ISSN 1070-4280, Russian Journal of Organic Chemistry, 2015, Vol. 51, No. 11, pp. 1668–1670. © Pleiades Publishing, Ltd., 2015. Original Russian Text © O.V. Ershov, V.N. Maksimova, M.Yu. Ievlev, M.Yu. Belikov, Kh.R. Khayarov, O.E. Nasakin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 11, pp. 1697–1699.