Skip to main content

A novel analogue of Asinger reaction for the synthesis of thiazinoquinoline derivatives

Abstract

The unexpected synthesis of 2H-[1,3]thiazino[6,5-b]quinoline derivatives from domino cyclic condensation of 2-mercaptoquinoline-3-carbaldehyde and ammonium acetate at ambient temperature in EtOH was described.

Graphical abstract

This is a preview of subscription content, access via your institution.

References

  1. Marco-Contelles J, Carreiras MD (2010) The Friedländer reaction. Lambert Academic, Saarbrücken

    Google Scholar 

  2. Marco-Contelles J, Perez-Mayoral E, Samadi A, Carreiras MD, Soriano E (2009) Chem Rev 109:2652

    CAS  Article  Google Scholar 

  3. Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z (2011) Adv Heterocycl Chem 185:139

    Article  Google Scholar 

  4. McCormick JL, McKee TC, Cardellina JH, Boyd MR (1996) J Nat Prod 59:469

    CAS  Article  Google Scholar 

  5. Majumdar KC, Chattopadhyay SK (2011) Heterocycles in natural product synthesis. Wiley, Weinheim

    Book  Google Scholar 

  6. Chan-Bacab MJ, Peña-Rodríguez LM (2001) Nat Prod Rep 18:674

    CAS  Article  Google Scholar 

  7. Solomon VR, Haq W, Srivastava K, Puri SK, Katti SB (2007) J Med Chem 50:394

    CAS  Article  Google Scholar 

  8. Paul N, Muthusubramanian S (2014) Med Chem Res 23:1612

    CAS  Article  Google Scholar 

  9. Salgueiro WG, Xavier MCDF, Duarte LFB, Camara DF, Fagundez DA, Soares ATG, Perin G, Alves D, Avila DS (2014) Eur J Med Chem 75:448

    CAS  Article  Google Scholar 

  10. O’Connor NA, López GE, Cruz A (2014) Curr Chem Lett 3:189

    Article  Google Scholar 

  11. Ghorab MM, Nassar OM, Hassan AY (1998) Phosphorus Sulfur Silicon Relat Elem 134:57

    Article  Google Scholar 

  12. Damanjit CS (2013) Pharmacophore 4:70 (and references therein)

    Google Scholar 

  13. Asinger F (1956) Angew Chem 68:377

    Article  Google Scholar 

  14. Asinger F, Thiel M (1958) Angew Chem 70:667

    CAS  Article  Google Scholar 

  15. Dömling A, Ugi I (1993) Tetrahedron 49:9495

    Article  Google Scholar 

  16. Dömling A, Bayler A, Ugi I (1995) Tetrahedron 51:755

    Article  Google Scholar 

  17. Sehlinger A, Stalling T, Martens J, Meier MAR (2014) Macromol Chem Phys 215:412

    CAS  Article  Google Scholar 

  18. Brockmeyer F, Schoemaker R, Schmidtmann M, Martens J (2014) Org Biomol Chem 12:5168

    CAS  Article  Google Scholar 

  19. Brockmeyer F, Gerven DV, Saak W, Martens J (2014) Synthesis 46:1603

    Article  Google Scholar 

  20. Liu Z-Q (2015) Curr Org Syn 12:20

    CAS  Article  Google Scholar 

  21. Toste FD, Lough LJ, Still IWJ (1995) Tetrahedron Lett 36:6619

    CAS  Article  Google Scholar 

  22. Still IWJ, Natividad-Preyra R, Toste FD (1999) Can J Chem 77:113

    CAS  Article  Google Scholar 

  23. Shiri M, Zolfigol MA, Pirveysian M, Ayazi-Nasrabadi R, Kruger HG, Naicker T, Mohammadpoor-Baltork I (2012) Tetrahedron 68:6059

    CAS  Article  Google Scholar 

  24. Zolfigol MA, Salehi P, Ghaderi A, Shiri M, Tanbakouchian Z (2006) J Mol Catal A Gen 259:253

    CAS  Article  Google Scholar 

  25. Zolfigol MA, Salehi P, Shiri M, Ghaderi A (2007) Catal Commun 8:1214

    CAS  Article  Google Scholar 

  26. Zolfigol MA, Salehi P, Ghaderi A, Shiri M (2007) J Chin Chem Soc 54:267

    CAS  Article  Google Scholar 

  27. Shiri M, Nejatinezhad-Arani A, Faghihi Z (2015) J Het Chem. doi:10.1002/jhet.2553

    Google Scholar 

  28. Zolfigol MA, Salehi P, Shiri M, Rastegar TF, Ghaderi A (2008) J Iran Chem Soc 5:490

    CAS  Article  Google Scholar 

  29. Hamidi H, Heravi MM, Tajbakhsh M, Shiri M, Oskooie HA, Shintre SA, Koorbanally NA (2015) J Iran Chem Soc 12:2205

    CAS  Article  Google Scholar 

  30. Srivastava A, Singh RM (2005) Indian J Chem B 44:1868

    Google Scholar 

Download references

Acknowledgments

We thank Alzahra University and Iran National Science Foundation (INSF) for financial support of our research group.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Morteza Shiri.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 936 kb)

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Faghihi, Z., Oskooie, H.A., Heravi, M.M. et al. A novel analogue of Asinger reaction for the synthesis of thiazinoquinoline derivatives. Monatsh Chem 148, 315–320 (2017). https://doi.org/10.1007/s00706-016-1755-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1755-1

Keywords

  • Cyclization
  • Condensation
  • 2-Mercaptoquinoline-3-carbaldehydes
  • Thiazinoquinoline
  • Catalyst-free
  • Asinger reaction