Abstract
Reaction of the available 1-tosyl-2,2-dichloroethenyl isothiocyanate with sodium cyanide yields new clearly electrophilic substrate of thiazole nature containing the nitrile group, the tosyl residue, and the chlorine atom at C2, C4, and C5 respectively. The direction of the reaction of this substrate with nucleophile depends significantly on the nature of the latter. It was used in regioselective syntheses of a series of the unknown previously trifunctional thiazoles.
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Babii, S.B., Zyabrev, V.S., and Drach, B.S., Zh. Obshch. Khim., 2002, vol. 72, no. 11, p. 1834.
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Turov, K.B. and Drach, B.S., Zh. Obshch. Khim., 2008, vol. 78, no.14, p. 648.
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Original Russian Text © K.V. Turov, T.K. Vinogradova, B.S. Drach, 2010, published in Zhurnal Obshchei Khimii, 2010, Vol. 80, No. 1, pp. 123–126.
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Turov, K.V., Vinogradova, T.K. & Drach, B.S. Synthesis of 4-tosyl-5-chloro-1,3-thiazole-2-carbonitrile and its transformations. Russ J Gen Chem 80, 117–120 (2010). https://doi.org/10.1134/S1070363210010159
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DOI: https://doi.org/10.1134/S1070363210010159