Skip to main content
Log in

Synthesis of 2-amino-4H-1,3-oxazines and 2-amino-4H-1,3-thiazines through a Yb(OTf)3-assisted, acid-catalyzed one-pot cyclocondensation reaction

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

An efficient synthesis of 2-amino-4,6-diaryl-4H-1,3-oxazine and 2-amino-4,6-diaryl-4H-1,3-thiazine derivatives has been demonstrated through a one-pot multicomponent cyclocondensation reaction. Ytterbium triflate and concentrated HCl has been utilized as the catalyst system for this reaction. The method produced good to excellent product yields and allowed a wide variation of the substituents in both aryl moieties.

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

Access this article

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

Instant access to the full article PDF.

Figure 1
Scheme 1

Similar content being viewed by others

References

  1. Mathew, B. P.; Kumar, A.; Sharma, S.; Shukla, P. K.; Nath, M. Eur. J. Med. Chem. 2010, 45, 1502.

    Article  CAS  Google Scholar 

  2. Cecchetti, V.; Cruciani, G.; Filipponi, E.; Fravolini, A.; Tabarrini, O.; Xin, T. Bioorg. Med. Chem. 1997, 5, 1339.

    Article  CAS  Google Scholar 

  3. Remillard, S.; Rebhun, L. I.; Howie, G. A.; Kupchan, S. M. Science 1975, 189, 1002.

    Article  CAS  Google Scholar 

  4. Sokolova, A. S.; Ryabokon', N. A.; Ershova, Yu. A.; Andreeva, N. A.; Nemeryuk, M. P.; Keremov, A. F.; Traven, N. I.; Yadrovskaya, V. A.; Chernov, V. A.; Safonova, T. S. Pharm. Chem. J. 1977, 11, 1205. [Khim.-Farm. Zh. 1977, 11(9), 49.]

  5. Haneishi, T.; Okazaki, T.; Hata, T.; Tamura, C.; Nomura, M.; Naito, A.; Seki, I.; Arai, M. J. Antibiot. 1971, 24, 797.

    Article  CAS  Google Scholar 

  6. Sasaki, K.; Kusakabe, Y.; Esumi, S. J. Antibiot. 1972, 25, 151.

    Article  CAS  Google Scholar 

  7. Young, S. D.; Britcher, S. F.; Tran, L. O.; Payne, L. S.; Lumma, W. C.; Lyle, T. A.; Huff, J. R.; Anderson, P. S.; Olsen, D. B.; Carroll, S. S.; Pettibone, D. J.; O'Brien, J. A.; Ball, R. G.; Balani, S. K.; Lin, J. H.; Chen, I.-W.; Schleif, W. A.; Sardana, V. V.; Long, W. J.; Byrnes, V. W.; Emini, E. A. Antimicrob. Agents Chemother. 1995, 39, 2602.

    Article  CAS  Google Scholar 

  8. Borroni, E.; Gobbi, L.; Hilpert, H.; Honer, M.; Muri, D.; Narquizian, R.; Polara, A. WO Patent 2012168175.

  9. Pietsch, M.; Gütschow, M. J. Med. Chem. 2005, 48, 8270.

    Article  CAS  Google Scholar 

  10. Yakovlev, I. P.; Prep'yalov, A. V.; Ivin, B. A. Chem. Heterocycl. Compd. 1994, 30, 255. [Khim. Geterotsikl. Soedin. 1994, 291.]

  11. Didwagh, S. S.; Piste, P. B. Int. J. Pharm. Sci. Res. 2013, 4, 2045.

    CAS  Google Scholar 

  12. Mironova, G. A.; Kuklin, V. N.; Kirillova, E. N.; Ivin, B. A. Chem. Heterocycl. Compd. 1986, 22, 1. [Khim. Geterotsikl. Soedin. 1986, 3.]

  13. Huang, S.; Pan, Y.; Zhu, Y.; Wu, A. Org. Lett. 2005, 7, 3797.

    Article  CAS  Google Scholar 

  14. Mandal, P. K.; Misra, A. K. Lett. Org. Chem. 2006, 3, 848.

    Article  CAS  Google Scholar 

  15. Kalirajan, R.; Sivakumar, S. U.; Jubie, S.; Gowramma, B.; Suresh, B. Int. J. ChemTech Res. 2009, 1, 27.

    CAS  Google Scholar 

  16. Kalirajan, R.; Kulshrestha, V.; Sankar, S.; Jubie, S. Eur. J. Med. Chem. 2012, 56, 217.

    Article  CAS  Google Scholar 

  17. Didwagh, S. S.; Piste, P. B. J. Chem. Pharm. Res. 2013, 5(5), 271.

    CAS  Google Scholar 

  18. Kobayashi, S.; Hachiya, I. J. Org. Chem. 1994, 59, 3590.

    Article  CAS  Google Scholar 

  19. Kobayashi, S.; Nagayama, S.; Busujima, T. J. Am. Chem. Soc. 1998, 120, 8287.

    Article  CAS  Google Scholar 

  20. Kobayashi, S. Pure Appl. Chem. 1998, 70, 1019.

    Article  CAS  Google Scholar 

  21. Kobayashi, S.; Manabe, K. Pure Appl. Chem. 2000, 72, 1373.

    Article  CAS  Google Scholar 

  22. Kumareswaran, R.; Shahi, S. P.; Rani, S.; Gupta, A.; Madhusudanan, K. P.; Vankar, Y. D. ARKIVOC 2002, (vii), 126.

  23. Salla, J. M.; Fernández-Francos, X.; Ramis, X.; Mas, C.; Mantecón, A.; Serra, A. J. Therm. Anal. Calorim. 2008, 91, 385.

    Article  CAS  Google Scholar 

  24. Dzudza, A.; Marks, T. J. J. Org. Chem. 2008, 73, 4004.

    Article  CAS  Google Scholar 

  25. Saito, T.; Kawamura, M.; Nishimura, J. Tetrahedron Lett. 1997, 38, 3231.

    Article  CAS  Google Scholar 

  26. Qian, C. T.; Wang, L. C.; Chen, R. F. Chin. J. Chem. 2001, 19, 419.

    Article  CAS  Google Scholar 

Download references

We gratefully acknowledge financial supports from Science and Engineering Research Board, DST, Goverment of India (SERB No.SR/FT/CS-116/2010) to AC and UGC for SRF fellowship to SP.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Arijit Chakraborty.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(8), 763–768

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary information file

(PDF 6652 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Putatunda, S., Chakraborty, A. Synthesis of 2-amino-4H-1,3-oxazines and 2-amino-4H-1,3-thiazines through a Yb(OTf)3-assisted, acid-catalyzed one-pot cyclocondensation reaction. Chem Heterocycl Comp 51, 763–768 (2015). https://doi.org/10.1007/s10593-015-1770-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-015-1770-x

Keywords

Navigation