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Synthesis of novel derivatives of 2-(azolylimino)thiazoline

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Abstract

Successive alkylation of 5-(3-phenylthioureido)-3H-imidazole-4-carboxamides with alkyl halides and chloroacetone gave (N-oxopropylimidazolyl)isothioureas, which were easily converted into derivatives of purine and imidazopyrazinone. In the case of ethyl 5-(3-phenylthioureido)-3H-imidazole-4-carboxylate, primary alkylation occurs at the N atom of the imidazole ring. Reactions of 5-(3-phenylthioureido)-3H-imidazole-4-carboxamides with haloketones afforded a number of 4-hydroxy-2-imidazolyliminothiazolidines and 2-imidazolylimino-Δ4-thiazolines.

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Authors and Affiliations

  1. Ural State Technical University, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    O. S. Eltsov & V. S. Mokrushin

  2. N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Division, Russian Academy of Sciences, 9 prosp. Akad. Lavrent’eva, 630090, Novosibirsk, Russian Federation

    A. V. Tkachev

Authors
  1. O. S. Eltsov
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  2. V. S. Mokrushin
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  3. A. V. Tkachev
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2196–2204, October, 2004.

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Eltsov, O.S., Mokrushin, V.S. & Tkachev, A.V. Synthesis of novel derivatives of 2-(azolylimino)thiazoline. Russ Chem Bull 53, 2293–2302 (2004). https://doi.org/10.1007/s11172-005-0116-8

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  • DOI: https://doi.org/10.1007/s11172-005-0116-8

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