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Modified Biginelli reaction in the synthesis of chromenopyrimidobenzimidazolones

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Abstract

Biginelli reaction of 4-hydroxychromen-2-one with aromatic aldehydes and biazanucleophiles was investigated. The character of the substituent in the aromatic aldehyde and the reaction conditions affect its direction. The possibility to separate two probable regio isomers and the preparation of the chromenopyrimidobenzimidazolone with angular junction was demonstrated. The use of nuclear Overhauser effect (NOE 1D) made it possible to establish the spatial interaction between ortho-protons of chromene and benzimidazole fragments additionally confirming the structure of the obtained compound. The identification of the possible intermediates in the case of reacting 3-methyl-1H-pyrazol-5-amine as the azabinucleophile confirms the assumed scheme of 2H-chromen-2-ones formation under the applied conditions.

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Authors and Affiliations

  1. Chemical Institute at Chernyshevskii Saratov State University, ul. Astrakhanskaya 83, Saratov, 410012, Russia

    O. A. Mazhukina, A. G. Platonova & O. V. Fedotova

  2. Physical and Chemical Institute at Ogarev Mordovian State University, Saransk, Russia

    V. A. Vasin

Authors
  1. O. A. Mazhukina
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  2. A. G. Platonova
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  3. O. V. Fedotova
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  4. V. A. Vasin
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Corresponding author

Correspondence to O. A. Mazhukina.

Additional information

Original Russian Text © O.A. Mazhukina, A.G. Platonova, O.V. Fedotova, V.A. Vasin, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 5, pp. 709–713.

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Mazhukina, O.A., Platonova, A.G., Fedotova, O.V. et al. Modified Biginelli reaction in the synthesis of chromenopyrimidobenzimidazolones. Russ J Org Chem 51, 691–696 (2015). https://doi.org/10.1134/S107042801505019X

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  • DOI: https://doi.org/10.1134/S107042801505019X

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