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Synthesis and reactions of 1-benzyl-3-haloalkyl-5-chloropyrazoles

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Abstract

Synthesized 1-benzyl-3-chloroalkyl-5-chloropyrazoles reacted with indole and pyrrole in DMSO in the presence of alkali to give 3-(heter-1-yl)alkyl-substituted 1-benzyl-5-chloropyrazoles. 1-[(1-Benzyl-5-chloropyrazol-3-yl)methyl]indole reacted regiospecifically with chloroal trifluoromethylsulfonyl- and 4-chlorophenylsulfonylimines providing the products of C-amidotrichloroethylation into the position 3 of the indole ring. {1-[(1-Benzyl-5-chloropyrazol-3-yl)methyl]indol-3-yl}sulfanylacetic acid was obtained by the reaction of 1-[(1-benzyl-5-chloropyrazol-3-yl)methyl]-indole with iodine, thiourea, and chloroacetic acid.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    E. V. Rudyakova, V. A. Savosik, I. T. Evstaf’eva, E. V. Kondrashov & G. G. Levkovskaya

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  1. E. V. Rudyakova
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  2. V. A. Savosik
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  3. I. T. Evstaf’eva
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  4. E. V. Kondrashov
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  5. G. G. Levkovskaya
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Correspondence to G. G. Levkovskaya.

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Original Russian Text © E.V. Rudyakova, V.A. Savosik, I.T. Evstaf’eva, E.V. Kondrashov, G.G. Levkovskaya, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 5, pp. 722–727.

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Rudyakova, E.V., Savosik, V.A., Evstaf’eva, I.T. et al. Synthesis and reactions of 1-benzyl-3-haloalkyl-5-chloropyrazoles. Russ J Org Chem 45, 705–711 (2009). https://doi.org/10.1134/S1070428009050108

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  • DOI: https://doi.org/10.1134/S1070428009050108

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