Skip to main content
SpringerLink
Log in

Synthesis, study of the structure, and modification of the products of the reaction of 4-aryl-4-oxobut-2-enoic acids with thiourea

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A number of previously undescribed derivatives of 2-amino-5-(2-aryl-2-oxoethyl)thiazol-4(5H)-one containing electron-donating substituents in the aromatic ring were synthesized by the reaction of (E)-4-aryl-4-oxobut-2-enoic acids with thiourea. Reduction of the reaction products with NaBH4 yielded diastereomeric alcohols, whereas bromination in AcOH was accompanied by elimination of HBr and the formation of (Z)-2-amino-5-(2-aryl-2-oxoethylidene)thiazol-4(5H)-ones.

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

Similar content being viewed by others

References

  1. Manjal, S. R.; Kaur, R.; Bratia, R.; Kumar, K.; Signh, V.; Shankar, R.; Kaur, R.; Raval, R. K. Вioorg. Chem. 2017, 75, 406.

    Google Scholar 

  2. Kaminskyy, D.; den Hartog, G. J. M.; Wojtyra, M.; Lelyukh, M.; Gzella, A.; Bast, A.; Lesyk, R. Eur. J. Med. Chem. 2016, 112, 180.

    Article  CAS  Google Scholar 

  3. Tripathi, A. C.; Gupta, S. J.; Fatima, G. N.; Sonar, P. K.; Verma, A.; Saraf, S. K. Eur. J. Med. Chem. 2014, 72, 52.

    Article  CAS  Google Scholar 

  4. Alwiswasy, R. M.; Jameel, R. M.; Hameed, B. J. Int. J. Res. Pharm. Sci. (Madurai, India) 2019, 10, 1763.

    Article  CAS  Google Scholar 

  5. Bayoumi, W. A.; Abdel-Rhman, S. H.; Shaker, M. E. Open Chem. J. 2014, 1, 33.

    Article  Google Scholar 

  6. Saeed, A.; Abbas, N.; Flörke, U. J. Braz. Chem. Soc. 2007, 18, 559.

    Article  CAS  Google Scholar 

  7. Liu, H.-L.; Li, Z.; Anthonsen, T. Molecules 2000, 5, 1055.

    Article  CAS  Google Scholar 

  8. Zarghi, A.; Najafnia, L.; Daraee, B.; Dadrass, O. G.; Hedayati, M. Bioorg. Med. Chem. Lett. 2007, 17, 5634.

    Article  CAS  Google Scholar 

  9. Appalanaidu, K.; Kotcherlakota, R.; Dadmal, T. L.; Bollu, V. S.; Kumbhare, R. M.; Patra, C. R. Bioorg. Med. Chem. Lett. 2016, 26, 5361.

    Article  CAS  Google Scholar 

  10. Küçükgüzel, İ.; Satılmış, G.; Gurukumar, K. R.; Basu, A.; Tatar, E.; Nichols, D. B.; Talele, T. T.; Kaushik-Basu, N. Eur. J. Med. Chem. 2013, 69, 931.

    Article  Google Scholar 

  11. Porshamsian, K.; Montazeri, N.; Rad-Moghadam, K.; Ali- Asgari, S. J. Heterocycl. Chem. 2010, 47, 1439.

  12. Metwally, M. A.; Farahat, A. A.; Abdel-Wahab, B. F. J. Sulfur Chem. 2010, 31, 315.

    Article  CAS  Google Scholar 

  13. Samala, G.; Madhuri, C.; Sridevi, P. J.; Nallangi, R.; Perumal, Y.; Dharmarajan, S. Eur. J. Chem. 2014, 5, 550.

    Article  Google Scholar 

  14. Haouas, B.; Sbei, N.; Ayari, H.; Benkhoud, M. L.; Batanero, B. New J. Chem. 2018, 42, 11776.

    Article  CAS  Google Scholar 

  15. Bougault, J.; Chabrier, P. Compt. Rend. 1947, 224, 656.

    CAS  Google Scholar 

  16. El-Sakka, S. S.; Soliman, M. H.; Abdullah, S. R. J. Chem. Sci. 2014, 1883.

  17. El-Hashash, M. A.; Essawy, A.; Fawzy, A. S. Adv. Chem. 2014, 619749.

  18. Abdel-Ghani, E. J. Chem. Res., Synop. 1999, 174.

  19. Salem, M. S.; Guirguis, D. B.; El-Helw, E. A. E.; Ghareeb, M. A.; Derbala, H. A. Y. Int. J. Sci. Res. 2014, 3(5), 1274.

  20. El-Aasar, N. K.; Saied, K. J. Heterocycl. Chem. 2008, 45, 645.

    Article  CAS  Google Scholar 

  21. Kaminskyy, D.; Den Hartog, G. J. M.; Wojtyra, M.; Lelyukh, M.; Gzella, A.; Bast, A.; Lesyk, R. Eur. J. Med. Chem. 2016, 112, 180.

    Article  CAS  Google Scholar 

  22. El-Mobayed, M. M.; Hussein, A. M.; Mohlhel, W. M. J. Heterocycl. Chem. 2010, 47, 534.

    CAS  Google Scholar 

  23. El-Hashash, M. A; Rizk, S. A.; Ahmed, E. A. Am. J. Chem. 2012, 2(1), 1.

  24. Khachikyan, R. Dzh.; Atashyan, S. M.; Agbalyan, S. G. Arm. Khim. Zhurn. 1981, 34, 775.

  25. Khachikyan, R. Dzh.; Grigoryan, R. T.; Atashyan, S. M.; Panosyan, G. А.; Agbalyan, S. G. Arm. Khim. Zhurn. 1984, 37, 237.

  26. El-Desuky, S.; El-Deen, I. M.; Abdel-Megid, M. J. Indian Chem. Soc. 1992, 69, 340.

    CAS  Google Scholar 

  27. Kolos, N. N.; Beryozkina, T. V.; Orlov, V. D. Heterocycles 2003, 60, 2115.

    Article  CAS  Google Scholar 

  28. Beryozkina, T. V.; Kolos, N. N.; Orlov, V. D.; Zubatyuk, R. I.; Shishkin, O. V. Phosphorus, Sulfur Silicon Relat. Elem. 2004, 179, 2153.

    Article  CAS  Google Scholar 

  29. Kolos, N. N.; Kovalenko, L. U.; Borovskoy, V. A. Chem. Heterocycl. Compd. 2011, 47, 983 [Khim. Geterotsikl. Soedin. 2011, 1198.]

  30. Yaseen, R.; Ekinci, D.; Senturk, M.; Hameed, A. D.; Ovais, S.; Rathore, P.; Samim, M.; Javed, K.; Supuran, C. T. Bioorg. Med. Chem. Lett. 2016, 26, 1337.

    Article  CAS  Google Scholar 

  31. El-Hashash, M. A; Abdel-Rahman, T. M.; Soliman, F. M. Boll. Chim. Farm. 1998, 137, 87.

    CAS  Google Scholar 

  32. Ramsh, S. M.; Smorygo, V. K.; Ginak, A. I. Chem. Heterocycl. Compd. 1984, 20, 865 [Khim. Geterotsikl. Soedin. 1984, 1066.]

  33. Espinosa, E.; Molins, E.; Lecomte, C. Chem. Phys. Lett. 1998, 285, 170.

    Article  CAS  Google Scholar 

  34. Kolos, N. N.; Kovalenko, L. Yu.; Kulikov, A. Yu. Russ. Chem.Bull. 2009, 58, 1041 [Izv. Akad. Nauk, Ser. Khim. 2009, 1014.]

  35. Wolinski, K.; Hinton. J. F.; Pulay, P. J. Am. Chem. Soc. 1990, 112, 8251.

    Article  CAS  Google Scholar 

  36. (а) Onoue, K.; Shintou, T.; Zhang, C. S.; Itoh, I. Chem. Lett. 2006, 35, 22. a Sonye, J. P.; Koide, K. J. Org. Chem. 2006, 71, 6254. b Runcie, K. A.; Taylor, R. J. K. Chem. Commun. 2002, 974.

  37. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Keith, T.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01; Gaussian, Inc.: Wallingford, 2010.

  38. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.

    Article  CAS  Google Scholar 

  39. Woon, D. E.; Dunning, T. H. J. Chem. Phys. 1993, 98, 1358.

    Article  CAS  Google Scholar 

  40. Bader, R. F. W. Chem. Rev. 1991, 91, 893.

    Article  CAS  Google Scholar 

  41. Bader, R. F. W. J. Phys. Chem. A 1998, 102, 7314.

    Article  CAS  Google Scholar 

  42. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. V. N. Karazin Kharkiv National University, 4 Svobody Sq, Kharkiv, 61022, Ukraine

    Nadezhda N. Kolos, Nikolai V. Nazarenko, Svetlana V. Shishkina, Andrey O. Doroshenko, Elena G. Shvets & Maksim A. Kolosov

  2. State Scientific Institution “Institute for Single Crystals”, National Academy of Sciences of Ukraine, 60 Nauky Ave, Kharkiv, 61001, Ukraine

    Svetlana V. Shishkina & Fedor G. Yaremenko

Authors
  1. Nadezhda N. Kolos
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nikolai V. Nazarenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Svetlana V. Shishkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Andrey O. Doroshenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Elena G. Shvets
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Maksim A. Kolosov
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Fedor G. Yaremenko
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Nadezhda N. Kolos.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(9), 1202–1209

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kolos, N.N., Nazarenko, N.V., Shishkina, S.V. et al. Synthesis, study of the structure, and modification of the products of the reaction of 4-aryl-4-oxobut-2-enoic acids with thiourea. Chem Heterocycl Comp 56, 1202–1209 (2020). https://doi.org/10.1007/s10593-020-02798-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-020-02798-y

Keywords

Search

Navigation