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Thiocyanation, Halogenation, Dehalogenation, Transhalogenation, and Nitration of 2-Substituted 4-(2-Furyl)thiazoles

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Abstract

Bromination and thiocyanation of 2-amino- and 2-acetylamino-4-(2-furyl)thiazoles when 1 mol of reagent is used at 10°C are directed to the 5 position. Formation of 5'-bromo-substituted derivatives when the reaction temperature is raised is the result of a secondary, thermodynamically controlled process. Monohalogenation and mononitration of 4-(2-furyl)-2-methylthiazole are directed to the 5' position. Nitration of 2-acetylamino-4-(5-nitro-2-furyl)thiazole by a nitrating mixture is accompanied by oxidative cleavage of the 5-nitrofuran moiety and leads to formation of 5,5'- and 3',5'-dinitro derivatives.

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Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga, LV-1006

    N. O. Saldabol, J. Popelis & V. Slavinska

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  1. N. O. Saldabol
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  2. J. Popelis
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  3. V. Slavinska
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Saldabol, N.O., Popelis, J. & Slavinska, V. Thiocyanation, Halogenation, Dehalogenation, Transhalogenation, and Nitration of 2-Substituted 4-(2-Furyl)thiazoles. Chemistry of Heterocyclic Compounds 38, 873–881 (2002). https://doi.org/10.1023/A:1020602308595

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