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Polyfunctional imidazoles: XIII.1 Addition and cyclization reactions of 1-aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles with sulfur and nitrogen nucleophiles

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Abstract

1-Aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles reacted with thiols and aromatic amines via Michael addition to give 5-[(1-arylsulfanyl)-2-nitroethyl)]-4-chloro-1H-imidazoles and N-[1-(1-aryl-4-chloro-1H-imidazol-5-yl)-2-nitroethyl]anilines, respectively. [2 + 3]-Cycloaddition of the title compounds to sodium azide afforded 4-(4-chloro-1H-imidazol-5-yl)-1H-1,2,3-triazoles.

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Authors and Affiliations

  1. Bukovinian State Medical University, Theatralna pl. 2, Chernivtsi, 58002, Ukraine

    V. A. Chornous & A. N. Grozav

  2. Ivano-Frankivsk National Medical University, Galitska ul. 2, Ivano-Frankivsk, 76018, Ukraine

    O. Ya. Mel’nik

  3. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, ul. Murmanskaya 5, Kiev, 02660, Ukraine

    S. Yu. Suikov & M. V. Vovk

Authors
  1. V. A. Chornous
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  2. O. Ya. Mel’nik
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  3. A. N. Grozav
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  4. S. Yu. Suikov
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  5. M. V. Vovk
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Corresponding author

Correspondence to M. V. Vovk.

Additional information

Original Russian Text © V.A. Chornous, O.Ya. Mel’nik, A.N. Grozav, S.Yu. Suikov, M.V. Vovk, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 3, pp. 408–412.

For communication XII, see [1].

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Chornous, V.A., Mel’nik, O.Y., Grozav, A.N. et al. Polyfunctional imidazoles: XIII.1 Addition and cyclization reactions of 1-aryl-4-chloro-5-(2-nitroethenyl)-1H-imidazoles with sulfur and nitrogen nucleophiles. Russ J Org Chem 53, 407–412 (2017). https://doi.org/10.1134/S1070428017030150

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  • DOI: https://doi.org/10.1134/S1070428017030150

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