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Nitration of 2- and 4-[2-(2-furyl)vinyl]thiazole derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Nitration of 4-methyl-2-[2-(nitro-2-furyl)vinyl]thiazole with a mixture of concentrated nitric and sulfuric acids leads to 4-methyl-5-nitro-2-[2-(3,5-dinitro-2-furyl)vinyl]thiazole. Under the same conditions 2-methyl- and 2-acetamido-4-[1-R-2-(5-nitro-2-furyl)vinyl]thiazoles (R=CH3, Cl) are nitrated in the 3 position of the furan ring, 2-amino-4-[1-chloro-2-(5-nitro-2-furyl)vinyl]thiazole is nitrated in the 5 position of the thiazole ring and 2-acetamido-5-nitro-4-[2-(2-furyl)vinyl]thiazole undergoes profound changes. Under the influence of a mixture of of nitric acid and acetic anhydride the latter compound is converted quantitatively to the 5-nitro derivative (with respect to the furan ring), whereas 4-[2-(5-nitro-2-furyl)vinyl]thiazole derivatives do not undergo reaction.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Academy of Sciences of the Latvian SSR, 226006, Riga

    N. O. Saldabol & Yu. Yu. Popelis

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  1. N. O. Saldabol
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  2. Yu. Yu. Popelis
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 314–317, March, 1977.

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Saldabol, N.O., Popelis, Y.Y. Nitration of 2- and 4-[2-(2-furyl)vinyl]thiazole derivatives. Chem Heterocycl Compd 13, 246–249 (1977). https://doi.org/10.1007/BF00470303

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  • DOI: https://doi.org/10.1007/BF00470303

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