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Regioselectivity of cyclization of 3-allyl(propargyl)sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles

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Chemistry of Heterocyclic Compounds Aims and scope

The interaction of 3-allylsulfanyl-5H-[1,2,4]triazino[5,6-b]indole with iodine led to 1-iodomethyl-1,2-dihydro[1,3]thiazolo[2',3':3,4][1,2,4]triazino[5,6-b]indol-11-ium pentaiodide with an angular structure, on the basis of which 1-iodomethyl-1,2-dihydro[1,3]thiazolo-, 1-methylidene-1,2-di-hydro[1,3]thiazolo, and 1-methyl[1,3]thiazolo derivatives were obtained. The intramolecular cyclization of 3-propargyl(allyl)sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles under the influence of concentrated sulfuric acid led to linear annelated products:3-methyl[1,3]thiazolo[3',2':2,3][1,2,4]tri-azino[5,6-b]indole or its 2,3-dihydro derivative.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ukraine National Academy of Sciences, 5 Murmanska St., Kyiv, 02094, Ukraine

    R. I. Vasˈkevich, A. I. Vasˈkevich, V. I. Staninets & M. V. Vovk

  2. Taras Shevchenko Kyiv National University, 64 Volodymyrska St., Kyiv, 01601, Ukraine

    A. V. Turov

Authors
  1. R. I. Vasˈkevich
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  2. A. I. Vasˈkevich
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  3. A. V. Turov
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  4. V. I. Staninets
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  5. M. V. Vovk
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Correspondence to R. I. Vasˈkevich.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, 1258–1263, August, 2011.

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Vasˈkevich, R.I., Vasˈkevich, A.I., Turov, A.V. et al. Regioselectivity of cyclization of 3-allyl(propargyl)sulfanyl-5H-[1,2,4]triazino[5,6-b]indoles. Chem Heterocycl Comp 47, 1037–1042 (2011). https://doi.org/10.1007/s10593-011-0871-4

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  • DOI: https://doi.org/10.1007/s10593-011-0871-4

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