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Synthesis of new imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one derivatives by iodocyclization of 6-alkenyl(alkynyl)-aminopyrazolo[3,4-d]pyrimidin-4(5H)-ones

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Abstract

6-Allyl(diallyl, prop-2-yn-1-yl)amino-1-R-pyrazolo[3,4-d]pyrimidin-4(5H)-ones reacted with iodine to give angularly fused 8-iodomethyl-7,8-dihydro-1-R-imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones which were treated with sodium acetate to obtain 8-methylidene-1-R-7,8-dihydroimidazo[1,2-a]pyrazolo-[4,3-e]pyrimidin-4(6H)-ones as a result of elimination of hydrogen iodide. 8-Methylidene-1-R-7,8-dihydroimidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones were converted into 8-methyl-1-R-imidazo[1,2-a]pyrazolo-[4,3-e]pyrimidin-4(5H)-ones on heating to the melting point. 8-Methylidene-1-phenyl-7,8-dihydroimidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one underwent isomerization into linearly fused 6-methyl-1-phenyl-1,8-dihydro-4H-imidazo[1,2-a]pyrazolo[3,4-d]pyrimidin-4-one on heating in sulfuric acid.

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Authors and Affiliations

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

    A. V. Bentya, R. I. Vas’kevich, E. B. Rusanov, M. V. Vovk & V. I. Staninets

  2. Taras Shevchenko Kiev National University, Kiev, Ukraine

    A. V. Turov

Authors
  1. A. V. Bentya
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  2. R. I. Vas’kevich
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  3. A. V. Turov
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  4. E. B. Rusanov
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  5. M. V. Vovk
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  6. V. I. Staninets
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Correspondence to A. V. Bentya.

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Original Russian Text © A.V. Bentya, R.I. Vas’kevich, A.V. Turov, E.B. Rusanov, M.V. Vovk, V.I. Staninets, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 7, pp. 1049–1056.

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Bentya, A.V., Vas’kevich, R.I., Turov, A.V. et al. Synthesis of new imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one derivatives by iodocyclization of 6-alkenyl(alkynyl)-aminopyrazolo[3,4-d]pyrimidin-4(5H)-ones. Russ J Org Chem 47, 1066–1073 (2011). https://doi.org/10.1134/S1070428011070165

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  • DOI: https://doi.org/10.1134/S1070428011070165

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