Skip to main content
SpringerLink
Log in

Synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A method for the synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils was developed based on nucleophilic substitution of the sulfur atom with the oxygen atom in the corresponding thioglycolurils via alkylation of the latter followed by acid hydrolysis of alkylsulfanyl derivatives of thioglycolurils, both with the isolation of alkylsulfanyl intermediates and by the one-pot method. The structure of the synthesized compounds was confirmed by X-ray structural analysis of several examples.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1.
Figure 2.
Figure 3.
Figure 4.
Figure 5.

Similar content being viewed by others

References

  1. (a) Thakral, S.; Singh, V. Curr. Bioact. Compd. 2019, 15, 316. (b) Suresh, A. S.; Baburajan, P.; Ahmed, M. Tetrahedron Lett. 2015, 56, 4864. (c) Boström, J.; Olsson, R. I.; Tholander, J.; Greasley, P. J.; Ryberg, E.; Nordberg, H.; Hjorth, S.; Cheng, L. Bioorg. Med. Chem. Lett. 2010, 20, 479. (d) Sun, H.-K.; Pang, A.; Farr, D. C.; Mosaiab, T.; Britton, W. J.; Anoopkumar-Dukie, S.; Grice, I. D.; Kiefel, M. J.; West, N. P.; Grant, G. D.; Houston T. A. Aust. J. Chem. 2018, 71, 716. (e) Verma, H.; Khatri, B.; Chakraborti, S.; Chatterjee, J. Chem. Sci. 2018, 9, 2443.

  2. (a) Fathalla, W.; Ali, I. A. I.; Pazdera, P. Beilstein J. Org. Chem. 2017, 13, 174. (b) Wiget, P. A.; Manzano, L. A.; Pruet, J. M.; Gao, G.; Saito, R.; Monzingo, A. F.; Jasheway, K. R.; Robertus, J. D.; Anslyn, E. V. Bioorg. Med. Chem. Lett. 2013, 23, 6799.

  3. (a) Xu, N.; Jin, X.; Suzuki, K.; Yamaguchi, K.; Mizuno, N. New J. Chem. 2016, 40, 4865. (b) Polushina, A. V.; Zavarzin, I. V.; Krayushkin, M. M.; Rodionova, G. M.; Yarovenko, V. N. Russ. Chem. Bull., Int. Ed. 2021, 70, 383. [Izv. Akad. Nauk, Ser. Khim. 2021, 383.] (c) Bao, X.; Wei, S.; Qian, X.; Qu, J.; Wang, B.; Zou, L.; Ge, G. Org. Lett. 2018, 20, 3394. (d) Beloglazkina, A.; Barashkin, A.; Polyakov, V.; Kotovsky, G.; Karpov, N.; Mefedova, S.; Zagribelny, B.; Ivanenkov, Y.; Kalinina, M.; Skvortsov, D.; Tafeenko, V.; Zyk, N.; Majouga, A.; Beloglazkina, E. Chem. Heterocycl. Compd. 2020, 56, 747. [Khim. Geterotsikl. Soedin. 2020, 56, 747.] (e) Perevoshchikova, A. N.; Eroshenko, D. V.; Dmitriev, M. V.; Grishko, V. V.; Shklyaev, Yu. V. J. Heterocycl. Chem. 2019, 56, 1634.

  4. (a) Mashkovskii, M. D. Lekarstvennye sredstva (Drugs [in Russian]); Moscow: Novaya volna, 2016, Vol. 1, p. 89. (b) Anikina, L. V.; Vikharev, Yu. B.; Baranov, V. V.; Malyshev, O. R.; Kravchenko, A. N. Mendeleev Commun. 2018, 28, 317. (c) Vikharev, Yu. B.; Anikina, P. V.; Chikunov, I. E.; Sigachev, А. S.; Kravchenko, А. N.; Shklyaev, Yu. V.; Makhova, N. N. Vopr. Biol. Med. Farm. Khimii 2006, (2), 12. (d) Anikina, L. V.; Gazieva, G. A.; Kravchenko, A. N. Russ. Chem. Bull., Int. Ed. 2020, 69, 563. [Izv. Akad. Nauk, Ser. Khim. 2020, 563.] (e) Bakibaev, A. A.; Akhmedzhanov, R. R.; Yagovkin, A. Yu.; Novozheeva, T. P.; Filimonov, V. D.; Saratikov, A. S. Pharm. Chem. J. 1993, 27, 401. [Khim. Farm. Zh. 1993, 27(6), 29.] (f) Kamburg, R. US Patent 20080227838; Chem. Abstr. 2008, 149, 347537. (g) Berlyand, A. S.; Prokopov, A. A. Pharm. Chem. J. 2014, 48, 347. [Khim. Farm. Zh. 2014, 48(5), 47.]

  5. (a) Gazieva, G. A.; Nechaeva, T. V.; Kostikova, N. N.; Sigay, N. V.; Serkov, S. A.; Popkov, S. V. Russ. Chem. Bull., Int. Ed. 2018, 67, 1059. [Izv. Akad. Nauk, Ser. Khim. 2018, 1059.] (b) Gazieva, G. A.; Anikina, L. V.; Nechaeva, T. V.; Pukhov, S. A.; Karpova, T. B.; Popkov, S. V.; Nelyubina, Yu. V.; Kolotyrkina, N. G.; Kravchenko, A. N. Eur. J. Med. Chem. 2017, 140, 141. (c) Gazieva, G. A.; Anikina, L. V.; Pukhov, S. A.; Karpova, T. B.; Nelyubina, Yu. V.; Kravchenko, A. N. Mol. Diversity 2016, 20, 837.

  6. Gazieva, G. A.; Vikharev, Yu. B.; Anikina, L. V.; Karpova, T. B.; Kravchenko, A. N.; Permyakov, E. A.; Svitanko, I. V. Mendeleev Commun. 2013, 23, 202.

  7. (a) Khan, S.; Tyagi, V.; Mahar, R.; Bajpai, V.; Kumar, B.; Chauhan, P. M. S. Synthesis 2013, 2405. (b) Izquierdo, J.; Etxabe, J.; Duñabeitia, E.; Landa, A.; Oiarbide, M.; Palomo, C. Chem.–Eur. J. 2018, 24, 7217. (c) Izquierdo, J.; Demurget, N.; Landa, A.; Brinck, T.; Mercero, J. M.; Diner, P.; Oiarbide, M.; Palomo, C. Chem.–Eur. J. 2019, 25, 12431.

  8. (a) Gazieva, G. A.; Poluboyarov, P. A.; Popov, L. D.; Kolotyrkina, N. G.; Kravchenko, A. N.; Makhova, N. N. Synthesis 2012, 3366. (b) Gazieva, G. A.; Karpova, T. B.; Popov, L. D.; Nelyubina, Yu. V.; Kravchenko, A. N. J. Heterocycl. Chem. 2015, 52, 1390.

  9. SDBSWeb. http://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and Technology, SDBS № 2699CDS-12-319). Accessed May 14, 2020.

  10. Panshina, S. Yu.; Ponomarenko, O. V.; Bakibaev, A. A.; Malkov, V. S. J. Struct. Chem. 2020, 61, 1315. [Zh. Strukt. Khim. 2020, 61, 1389.]

  11. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Adv. 2015, A71, 3.

  12. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave, Moscow, 119991, Russia

    Sergei А. Serkov, Marina А. Es’kova, Natalya V. Sigay, Natalya N. Kostikova, Natalya G. Kolotyrkina & Galina А. Gazieva

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, Moscow, 119991, Russia

    Marina А. Es’kova & Tatyana N. Volkhina

  3. D. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq, Moscow, 125047, Russia

    Tatyana N. Volkhina

Authors
  1. Sergei А. Serkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Marina А. Es’kova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Natalya V. Sigay
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Natalya N. Kostikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Tatyana N. Volkhina
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Natalya G. Kolotyrkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Galina А. Gazieva
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Galina А. Gazieva.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(6), 646–655

Supplementary Information

ESM 1

(PDF 4926 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Serkov, S.А., Es’kova, M.А., Sigay, N.V. et al. Synthesis of 1,3-dialkyl-4-[(arylmethylidene)amino]glycolurils. Chem Heterocycl Comp 57, 646–655 (2021). https://doi.org/10.1007/s10593-021-02963-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-02963-x

Keywords

Search

Navigation