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Synthesis and Structure of 5-Indolyl-6-thienyl-1,2,4-triazines

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Abstract

Acylation of indole and 2,5-dimethylthiophene with 2-(3-indolyl)-2-oxoacetyl chloride afforded the corresponding diketones. 1-(2,5-Dimethyl-3-thienyl)-2-(3-indolyl)ethanedione reacted with thiosemicarbazide under atmosperic and elevated pressure to give 6-(2,5-dimethyl-3-thienyl)-5-(3-indolyl)-2,3-dihydro-1,2,4-triazine-3-thione whose structure was studied in detail by the X-ray diffraction method. Reactions of 6-(2,5-dimethyl-3-thienyl)-5-(3-indolyl)-2,3-dihydro-1,2,4-triazine-3-thione with amines and hydrazine resulted in formation of fused triazolo- and tetrazolotriazines.

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Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    M. M. Krayushkin, V. N. Yarovenko, I. P. Sedishev, I. V. Zavarzin & L. G. Vorontsova

  2. Nesmeyanov Institute of Organometallic Compounds, Russian Academy of Sciences, Moscow, Russia

    Z. A. Starikova

Authors
  1. M. M. Krayushkin
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  2. V. N. Yarovenko
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  3. I. P. Sedishev
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  4. I. V. Zavarzin
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  5. L. G. Vorontsova
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  6. Z. A. Starikova
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Dedicated to Full Member of the Russian Academy of Sciences V.I. Minkin on his Jubilee

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Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 895–902.

Original Russian Text Copyright © 2005 by Krayushkin, Yarovenko, Sedishev, Zavarzin, Vorontsova, Starikova.

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Krayushkin, M.M., Yarovenko, V.N., Sedishev, I.P. et al. Synthesis and Structure of 5-Indolyl-6-thienyl-1,2,4-triazines. Russ J Org Chem 41, 875–883 (2005). https://doi.org/10.1007/s11178-005-0258-z

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  • DOI: https://doi.org/10.1007/s11178-005-0258-z

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