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Domino reactions of 3-methyl-5-aminopyrazole with aryl(hetaryl)aldehydes, cyclopentanone, cyclopentan-1,3-dione, and 1,3-indanedione

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Abstract

Domino reactions of 3-methylpyrazol-5-amine with aromatic or heterocyclic aldehydes, cyclopentanone, cyclopentane-1,3-dione or indane-1,3-dione in DMF or in alcoholic medium proceed regioselectively and lead to the formation of partially hydrogenated 4-aryl(hetaryl)-substituted cyclopenta[d]-pyrazolo[3,4-b]pyridine, cyclopenta[b]pyrazolo[4,3-e]pyridin-5(2H)-one or indeno[1,2-b]pyrazolo[4,3-e]pyridin-5(2H)-one systems respectively. The structure of 3-methyl-4-phenyl-2,5,6,7-tetrahydrocyclopenta[b]pyrazolo[ 4,3-e]pyridine and 3-methyl-4-(4-fluorophenyl)-4,6,7,8-tetrahydro-cyclopenta[b]pyrazolo[4,3-e]pyridin-5(2H)-one was confirmed by X-ray diffraction (XRD).

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Authors and Affiliations

  1. Danilevskii Institute of Problems of Endocrine Pathology, National Academy of Medical Sciences of Ukraine, ul. Artema 10, Kharkiv, 61002, Ukraine

    V. V. Lipson, N. I. Zemlyanaya, M. G. Shirobokova, V. I. Musatov, S. V. Shishkina & D. S. Sofronov

  2. Institute of Single Crystals, National Academy of Sciences of Ukraine, Kharkiv, Ukraine

    V. V. Lipson, V. V. Borodina & N. I. Zemlyanaya

  3. Karazin Kharkiv National University, Kharkiv, Ukraine

    V. V. Lipson & S. V. Shishkina

Authors
  1. V. V. Lipson
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  2. V. V. Borodina
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  3. N. I. Zemlyanaya
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  4. M. G. Shirobokova
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  5. V. I. Musatov
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  6. S. V. Shishkina
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  7. D. S. Sofronov
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Correspondence to V. V. Lipson.

Additional information

Original Russian Text © V.V. Lipson, V.V. Borodina, N.I. Zemlyanaya, M.G. Shirobokova, V.I. Musatov, S.V. Shishkina, D.S. Sofronov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 714–721.

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Lipson, V.V., Borodina, V.V., Zemlyanaya, N.I. et al. Domino reactions of 3-methyl-5-aminopyrazole with aryl(hetaryl)aldehydes, cyclopentanone, cyclopentan-1,3-dione, and 1,3-indanedione. Russ J Org Chem 51, 697–704 (2015). https://doi.org/10.1134/S1070428015050206

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  • DOI: https://doi.org/10.1134/S1070428015050206

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