Skip to main content
SpringerLink
Log in

Polyethylene glycol (PEG-400) promoted one-pot, five-component synthesis of (E)-ethyl2-(2-((E)-2-(1-(4-methyl-2-(phenylamino)thiazol-5yl)ethylidene)hydrazinyl)-4-oxothiazol-5(4H)-ylidene)acetates

  • Original Article
  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

A facile, inexpensive and eco-friendly synthesis of functionalised (E)-ethyl2-(2-((E)-2-(1-(4-methyl-2-(phenylamino)thiazol-5yl)ethylidene)hydrazinyl)14-oxothiazol-5(4H)-ylidene)acetates has been developed via one-pot five-component approach. The title compounds were synthesized by the reaction of anilines, 3-chloropentane-2,4-dione, ammoniumthiocyanate, thiosemicarbazide and dialkylacetylene dicarboxylate using polyethylene glycol as green and recyclable solvent. The domino reaction proceeded smoothly in good-to-excellent yields.

Graphical abstract

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

Fig. 1
Scheme 1
Scheme 2
Scheme 3

Similar content being viewed by others

References

  1. Alsharif ZA, Alam MA (2017) Modular synthesis of thiazoline and thiazole derivatives by using a cascade protocol. RSC Adv 7:32647–32651

    Article  CAS  Google Scholar 

  2. de Santana TL, Barbosa MO, Gomes PATM, da Cruz ACN, da Silva TG, Leite ACL (2018) Synthesis, anticancer activity and mechanism of action of new thiazole derivatives. Eur J Med Chem 144:874–886

    Article  Google Scholar 

  3. Sinha S, Doble M, Manju SL (2018) Design, synthesis and identification of novel substituted 2-amino thiazole analogues as potential anti-inflammatory agents targeting 5-lipoxygenase. Eur J Med Chem 158:34–50

    Article  CAS  Google Scholar 

  4. Lino CI, de Souza IG, Borelli BM, Matos TTS, Teixeira INS, Ramos JP, de Souza Fagundes EM, Fernandes PO, Maltarollo VG, Johann S, de Oliveira RB (2018) Synthesis, molecular modeling studies and evaluation of antifungal activity of a novel series of thiazole derivatives. Eur J Med Chem 151:248–260

    Article  CAS  Google Scholar 

  5. Sharma SK, Tandon M, Lown JW (2000) Design and synthesis of novel thiazole-containing cross-linked polyamides related to the antiviral antibiotic distamycin. J Org Chem 65(4):1102–1107

    Article  CAS  Google Scholar 

  6. Karuvalam RP, Haridas KR, Nayak SK, Guru Row TN, Rajeesh P, Rishikesan R, Kumari NS (2012) Design, synthesis of some new (2-aminothiazol-4-yl)methylester derivatives as possible antimicrobial and antitubercular agents. Eur J Med Chem 49:172–182

    Article  CAS  Google Scholar 

  7. Kumawat MK (2018) Thiazole containing heterocycles with antimalarial activity. Curr Drug Discov Technol 15:196–200

    Article  CAS  Google Scholar 

  8. Maillard LT, Bertout S, Quinonero O, Akalin G, Turan-Zitouni G, Fulcrand P, Demirci F, Martinez J, Masurier N (2013) Synthesis and anti-Candida activity of novel 2-hydrazino-1,3-thiazole derivatives. Bioorg Med Chem Lett 23:1803–1807

    Article  CAS  Google Scholar 

  9. Hai-Bo S, Shi-Jie Z, Qiu-Fu G, Dian-Wu G, Chao-Ming C, Wei-Xiao H (2010) Synthesis and anticancer evaluation of thiazolyl-chalcones. Bioorg Med Chem Lett 20:6555–6559

    Article  Google Scholar 

  10. Sucheta, Tahlan S, Verma PK (2017) Biological potential of thiazolidinedione derivatives of synthetic origin. Chem Cent J 11:130

    Article  CAS  Google Scholar 

  11. Apostolidis I, Liaras K, Geronikaki A, Hadjipavlou-Litina D, Gavalas A, Sokovic M, Glamoclija J, Ciric AC (2013) Synthesis and biological evaluation of some 5-arylidene-2-(1,3-thiazol-2-ylimino)-1,3-thiazolidin-4-ones as dual anti-inflammatory/antimicrobial agents. Bioorg Med Chem 21:532–539

    Article  CAS  Google Scholar 

  12. Kouatli O, Athina G, Panagiotis Z, Charalabos C, Marina S, Ana C, Jasmina G (2010) Novel 4-thiazolidinone derivatives as potential antifungal and antibacterial drugs. Bioorg Med Chem 18:426–432

    Article  Google Scholar 

  13. Saeed A, Al-Masoudi NA, Latif M (2013) Synthesis and antiviral activity of new substituted methyl [2-(arylmethylene-hydrazino)-4-oxo-thiazolidin-5-ylidene]acetates. Arch Pharm Chem Life Sci 346:618–625

    Article  CAS  Google Scholar 

  14. Asghari A, Pourshab M, Mohseni M (2018) Synthesis, characterization, and evaluation of antioxidant and antibacterial activities of novel indole-hydrazono thiazolidinones. Monatsh Chem Chem Mon 149:2327–2336

    Article  CAS  Google Scholar 

  15. Rojas Ruiz FA, Garcia-Sanchez RN, Estupinan SV, Gomez-Barrio A, Torres Amado DF, Perez-Solorzano BM, Nogal-Ruiz JJ, Martinez-Fernandez AR, Kouznetsov VV (2011) Synthesis and antimalarial activity of new heterocyclic hybrids based on chloroquine and thiazolidinone scaffolds. Bioorg Med Chem 19:4562–4573

    Article  CAS  Google Scholar 

  16. Liaras K, Fesatidou M, Geronikaki A (2018) Thiazoles and thiazolidinones as COX/LOX inhibitors. Molecules 23:685

    Article  Google Scholar 

  17. Bondock S, Khalifa W, Fadda AA (2007) Synthesis and antimicrobial evaluation of some new thiazole, thiazolidinone and thiazoline derivatives starting from 1-chloro-3,4-dihydronaphthalene-2-carboxaldehyde. Eur J Med Chem 42:948–954

    Article  CAS  Google Scholar 

  18. Domling A (2006) Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chem Rev 106:17–89

    Article  Google Scholar 

  19. Zhu J, Bienaym H (2005) Multicomponent reactions. Wiley-VCH, Weinheim

    Book  Google Scholar 

  20. Tietze LF, Brasche G, Gericke KM (2006) Domino reactions in organic synthesis. Wiley-VCH, Weinheim

    Book  Google Scholar 

  21. Ibarra IA, Islas-Jacome A, Gonzalez-Zamora E (2018) Synthesis of polyheterocycles via multicomponent reactions. Org Biomol Chem 16:1402–1418

    Article  CAS  Google Scholar 

  22. Chandrasekhar S, Narsihmulu Ch, Shameem Sultana S, Ramakrishna Reddy N (2002) Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction. Org. Lett. 4(25):4399–4401

    Article  CAS  Google Scholar 

  23. Sujatha K, Vedula RR (2018) Novel one-pot expeditious synthesis of 2,4-disubstituted thiazoles through a three component reaction under solvent free conditions. Synth Commun 48:302–308

    Article  CAS  Google Scholar 

  24. Sujatha K, Deshpande RP, Kesharwani RK, Prakash Babu P, Vedula RR (2019) An efficient one-pot expeditious synthesis of 3-phenyl-1-(6-phenyl-7H-[1, 2, 4] triazolo[3,4-b][1, 3, 4] thiadiazin-3-yl)-1H-pyrazol-5-amines via multicomponent approach. Synth Commun 49:49–55

    Article  CAS  Google Scholar 

  25. Sujatha K, Vedula RR (2019) Multicomponent efficient synthesis of new [1, 2, 4]triazolo[3, 4] thiadiazines. J Heterocycl Chem 56:832–838

    Article  CAS  Google Scholar 

  26. Hai-Bo S, Shi-Jie Z, Yan-Fang L, Wei-Xiao H, Chao-Ming C (2011) Study on condensation of N-aryl thioureas with 3-bromo-acetylacetone: synthesis of aminothiazoles and iminodihydrothiazoles, and their in vitro antiproliferative activity on human cervical cancer cells. J Hetrocycl Chem 48:1061–1066

    Article  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the Director of the National Institute of Technology, Warangal Telangana, India, for providing financial support and facilities.

Author information

Authors and Affiliations

  1. Department of Chemistry, National Institute of Technology, Warangal, Telangana, 506 004, India

    Kodam Sujatha & Rajeswar Rao Vedula

Authors
  1. Kodam Sujatha
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Rajeswar Rao Vedula
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Rajeswar Rao Vedula.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 5058 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sujatha, K., Vedula, R.R. Polyethylene glycol (PEG-400) promoted one-pot, five-component synthesis of (E)-ethyl2-(2-((E)-2-(1-(4-methyl-2-(phenylamino)thiazol-5yl)ethylidene)hydrazinyl)-4-oxothiazol-5(4H)-ylidene)acetates. Mol Divers 24, 413–421 (2020). https://doi.org/10.1007/s11030-019-09962-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11030-019-09962-3

Keywords

Search

Navigation