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Efficient synthesis of substituted 8-(pyrazolo[3,4-d]pyrimidin-6-yl)-1,2-dihydroquinolines

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Chemistry of Heterocyclic Compounds Aims and scope

An effective method for the synthesis of 8-(1-aryl-4-methoxy-1Н-pyrazolo[3,4-d]pyrimidin-6-yl)-2,2,4-trimethyl-1,2-dihydroquinolines was developed on the basis of a three-component reaction between substituted 4,4,6-trimethyl-4H-pyrrolo[3,2,1-ij]quinoline-1,2-diones and 5-amino-1-aryl-1H-pyrazole-4-carbonitriles in refluxing methanol in the presence of an excess of sodium methoxide. HPLC-MS analysis showed that the cascade process started by addition of methanol molecule to the nitrile group of aminopyrazolecarbonitrile.

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This work received financial support from the Ministry of Education and Science Russian Federation within the framework of State Contract with universities regarding scientific research during years 2017–2019 (project No. 4.3633.2017/4.6).

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya Sq., Voronezh, 394018, Russia

    Svetlana M. Medvedeva, Yevgeniya A. Kosheleva, Mariya A. Berdnikova & Khidmet S. Shikhaliev

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  1. Svetlana M. Medvedeva
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  2. Yevgeniya A. Kosheleva
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  3. Mariya A. Berdnikova
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  4. Khidmet S. Shikhaliev
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Corresponding author

Correspondence to Khidmet S. Shikhaliev.

Additional information

The Supplementary information file containing 1Н and 13С NMR spectra and mass spectra of compounds 3a–e, as well as the results of HPLC-MS analyses of reaction mixture during the synthesis of compound 3d is available at the journal website at http://link.springer.com/journal/10593.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(8), 784–788

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Medvedeva, S.M., Kosheleva, Y.A., Berdnikova, M.A. et al. Efficient synthesis of substituted 8-(pyrazolo[3,4-d]pyrimidin-6-yl)-1,2-dihydroquinolines. Chem Heterocycl Comp 54, 784–788 (2018). https://doi.org/10.1007/s10593-018-2351-6

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  • DOI: https://doi.org/10.1007/s10593-018-2351-6

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