Izvestiya of Saratov University.

Chemistry. Biology. Ecology

ISSN 1816-9775 (Print)
ISSN 2541-8971 (Online)

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Tikhomolova A. S., Mayorova O. A., Yegorova A. Y. Synthesis and structural features of 5-(4-bromophenyl)-3-((6-amino-2-mercaptopyrimidine)-4-amino))methylidene)-3Н-furan-2-one. Izvestiya of Saratov University. Chemistry. Biology. Ecology, 2022, vol. 22, iss. 1, pp. 4-8. DOI: 10.18500/1816-9775-2022-22-1-4-8

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Synthesis and structural features of 5-(4-bromophenyl)-3-((6-amino-2-mercaptopyrimidine)-4-amino))methylidene)-3Н-furan-2-one

Tikhomolova Alexandra S., Saratov State University
Mayorova Oksana Aleksandrovna, Saratov State University
Yegorova Alevtina Yu., Saratov State University

This work shows the possibility of synthesizing previously unknown 5-(4-bromophenyl)-3-((6-amino-2-mercaptopyrimidine)-4-amino)) methylidene-3H-furan-2-one containing a pharmacophore pyrimidine fragment by four-component one-pot reaction of malononitrile as the second methylene active component, thiourea, orthoester and 5-(4-bromophenyl)-3H-furan-2-one, which proceeds under mild conditions during thermal activation of the reaction mixture in isopropyl alcohol. Orthoester, as an electrophilic particle, makes it possible to introduce an additional carbon atom into the structure. The amino component was mercaptodiaminopyrimidine, which is formed in situ during the transformation by the condensation of malononitrile and thiourea. The composition and structure of the product was established using the methods of elemental analysis, IR and complex NMR spectroscopy data. It has been revealed that 5-(4-bromophenyl)-3-((6-amino-2-mercaptopyrimidine)-4-amino))- methylidene)-3Н-furan-2-one in KBr matrix and in solution exists as a mixture Z- and E-enamines, with a predominance of the E-conformer. This is evidenced by the duplication of signals in the 1 H NMR spectrum of the protons of the exocyclic and furan-2-one fragments and doublets of NH-protons. Based on the experimental data obtained, a scheme for the formation of the target system is proposed. It has been found that the reaction can proceed along two equally probable pathways through the ethoxymethylene derivative (path A) or with the formation of an ethoxyimine intermediate (path B).

  1. Dong Y., Shi Q., Liu Y.-N., Wang X., Bastow K. F., Lee K.-H. Antitumor Agents. 266. Design, synthesis, and biological evaluation of novel 2-(furan-2-yl)naphthalen-1-ol derivatives as potent and selective antibreast cancer agents // J. Med. Chem. 2009. Vol. 52, № 11. P. 3586–3590. https://doi.org/10.1021/jm9001567
  2. Wellington K. W., Qwebani-Ogunleye T., Kolesnikova N. I., Brady, D., Koning C. B. de. One-Pot laccase-catalysed synthesis of 5,6-dihydroxylated benzo[b]furans and catechol derivatives, and their anticancer activity // Archiv Der Pharmazie. 2013. Vol. 346, № 4. P. 266–277. https://doi.org/10.1002/ardp.201200413
  3. Hashem A. I., Youssef A. S. A., Kandeel K. A., AbouElmagd W. S. I. Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activity // Eur. J. Med. Chem. 2007. Vol. 42, № 7. P. 934–939. https://doi.org/10.1016/j.ejmech.2006.12.032
  4. Abou-Elmagd W. S. I., Hashem A. I. Synthesis and antitumor activity evaluation of some novel-fused and spiro heterocycles derived from a 2(3H)-furanone derivative // J. Heterocycl. Chem. 2015. Vol. 53, № 1. P. 202–208. https://doi.org/10.1002/jhet.2401
  5. Alam M. M., Husain A., Hasan S. M., Suruchi T. Synthesis and pharmacological evaluation of 2(3H)-furanones and 2(3H)-pyrrolones, combining analgesic and antiinfl ammatory properties with reduced gastrointestinal toxicity and lipid peroxidation // Eur. J. Med. Chem. 2009. Vol. 44, № 6. P. 2636–2642. https://doi.org/10.1016/j.ejmech.2008.10.030
  6. Mohareb R. M., Manhi F. M., Mahmoud M. A. A., Abdelwahab A. Uses of dimedone to synthesis pyrazole, isoxazole and thiophene derivatives with antiproliferative, tyrosine kinase and Pim-1 kinase inhibitions // Med. Chem. Res. 2020. Vol. 29. P. 1536–1551. https://doi.org/10.1007/s00044-020-02579-4
  7. Mpitimpiti A. N., Petzer J. P., Petzer A., Jordaan J. H. L., Lourens A. C. U. Synthesis and evaluation of chromone derivatives as inhibitors of monoamine oxidase // Molecular Diversity. 2019. Vol. 23, № 4. P. 897–913. https://doi.org/10.1007/s11030-019-09917-8
  8. 8. Osipov A. K., Anis’kov A. A., Grinev V. S., Yegorova A. Y. Study of E/Z isomerization of (arylamino)methylidenefuran-2(3H)-ones by 1H, 13C, 15N spectroscopy and DFT calculations in different solvents // Magnetic Resonance in Chemistry. 2017. Vol. 55, № 8. P. 730–737. https://doi.org/10.1002/mrc.4583
  9. Osipov A. K., Anis’kov A. A., Yegorova A. Y. Synthesis and confi guration of (arylamino)methylidene-3H-furan2-ones. Russian Journal of Organic Chemistry, vol. 53, iss. 2, pp. 210–214 (in Russian). https://doi.org/10.1134/s1070428017020117