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Synthesis of New Polyheterocyclic Compounds Based on Chalcones

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Abstract

The reaction of methyl N-{4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetyl]phenyl}carbamate with tosylmethyl isocyanide in tetrahydrofuran in the presence of potassium tert-butoxide led to the formation of methyl N-{4-[(4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinolin-1-yl)carbonyl]phenyl}carbamate. Three-component condensation of methyl N-{4-[(E)-3-R-prop-2-enoyl]phenyl}carbamates and methyl N-{4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)acetyl]phenyl}carbamate with sarcosine and paraformaldehyde in boiling toluene with simultaneous removal of water by azeotropic distillation afforded methyl N-(4-{4-[4-R-1-methyl-pyrrolidin-3-yl]carbonyl}phenyl)carbamates and methyl N-[4-(1′-methyl-2-oxo-1,2-dihydrospiro[indole-3,3′-pyrrolidin]-4′-ylcarbonyl)phenyl]carbamate, respectively.

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Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 4.9288.2017BCh) and by the Russian Foundation for Basic Research (project no. 19-03-00006A).

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Authors and Affiliations

  1. Astrakhan State University, Astrakhan, Russia

    A. V. Velikorodov & N. N. Stepkina

  2. Astrakhan State Technical University, Astrakhan, Russia

    M. A. Polovinkina & V. P. Osipova

Authors
  1. A. V. Velikorodov
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  2. N. N. Stepkina
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  3. M. A. Polovinkina
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  4. V. P. Osipova
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Corresponding author

Correspondence to A. V. Velikorodov.

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Conflict of Interests

The authors declare the absence of conflict of interests.

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 7, pp. 1103–1109.

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Velikorodov, A.V., Stepkina, N.N., Polovinkina, M.A. et al. Synthesis of New Polyheterocyclic Compounds Based on Chalcones. Russ J Org Chem 55, 999–1004 (2019). https://doi.org/10.1134/S1070428019070157

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  • DOI: https://doi.org/10.1134/S1070428019070157

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