Skip to main content
Log in

Use of Hypervalent Iodine in the Synthesis of Isomeric Dihydrooxazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

A Correction to this article was published on 01 June 2018

This article has been updated

A convenient synthesis of 2- and/or 3-oxazolines has been developed depending on the structure and stereochemistry of the starting amino alcohol. PhI(OAc)2 acted as oxidant on the intermediate imine, as supported by NMR investigation. The findings demonstrate a new route providing access to unusual 3-oxazolines.

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.
Figure 2.
Figure 3.

Similar content being viewed by others

Change history

  • 04 August 2018

    The name of author "Giuseppe Ronamazzi" should read "Giuseppe Romanazzi".

References

  1. Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis; Wirth, T., Ed.; Springer: Berlin, 2003.

  2. Zheng, Z.; Ma, S.; Tang, L.; Zhang-Negrerie, D.; Du, Y.; Zhao, K. J. Org. Chem. 2014, 79, 4687.

    Article  CAS  PubMed  Google Scholar 

  3. Du, Y.; Liu, R.; Linn, G.; Zhao, K. Org. Lett. 2006, 8, 5919.

    Article  CAS  PubMed  Google Scholar 

  4. Serna, S.; Tellitu, I.; Domínguez, E.; Moreno, I.; San Martín, R. Org. Lett. 2005, 7, 3073.

    Article  CAS  PubMed  Google Scholar 

  5. Das, B.; Srinivas, Y.; Holla, H.; Krishnaiah, M.; Narender, R. Chem. Lett. 2007, 36, 1270.

    Article  CAS  Google Scholar 

  6. Naganaboina, R. T.; Peddinti, R. K. Tetrahedron 2015, 71, 6245.u

  7. Prajapati, N. P.; Vekariya, R. H.; Borad, M. A.; Patel, H. D. RSC Adv. 2014, 4, 60176.

    Article  CAS  Google Scholar 

  8. Ranjith, J.; Rajesh, N.; Sridhar, B.; Krishna, P. R. Org. Biomol. Chem. 2016, 14, 10074.

    Article  CAS  PubMed  Google Scholar 

  9. (a) Saikia, U. P.; Baruah, D.; Pahari, P.; Borah, M. J.; Goswami, A.; Konwar, D. Tetrahedron Lett. 2014, 55, 4328. (b) Liu, G.-Q.; Yang, C.-H; Li, Y.-M. J. Org. Chem. 2015, 80, 11339.

  10. For other examples on 2-oxazolines: (a) Degennaro, L.; Mansueto, R.; Carenza, E.; Rizzi, R.; Florio, S.; Pratt, L. M.; Luisi, R. Chem.–Eur. J. 2011, 17, 4992. (b) Luisi R.; Capriati, V.; Florio, S.; Vista, T. J. Org. Chem. 2003, 68, 9861. (c) Degennaro, L.; Capriati, V.; Carlucci, C.; Florio, S.; Luisi R.; Nuzzo, I.; Cuocci, C. Tetrahedron 2009, 65, 8745.

  11. Karade, N. N.; Tiwari, G. B.; Gampawar, S. V. Synlett 2007, 1921.

  12. Murai, K.; Takahara, Y.; Matsushita, T.; Komatsu, H.; Fujioka, H. Org. Lett. 2010, 12, 3456.

    Article  CAS  PubMed  Google Scholar 

  13. Zeng, T.-T.; Xuan, J.; Ding, W.; Wang, K.; Lu, L.-Q.; Xiao, W.-J. Org. Lett. 2015, 17, 4070.

    Article  CAS  PubMed  Google Scholar 

  14. Varma, R. S.; Saini, R. K.; Prakash, O. Tetrahedron Lett. 1997, 38, 2621.

    Article  CAS  Google Scholar 

  15. Koleda, O.; Broese, T.; Noetzel, J.; Roemelt, M.; Suna, E.; Francke, R. J. Org. Chem. 2017, 82, 11669.

    Article  CAS  PubMed  Google Scholar 

  16. Zhong, C. L.; Tang, B. Y.; Yin, P.; Chen, Y.; He, L. J. Org. Chem. 2012, 77, 4271.

    Article  CAS  PubMed  Google Scholar 

  17. Minakata, S.; Morino, Y.; Ide, T.; Oderaotoshi, Y.; Komatsu, M. Chem. Commun. 2007, 31, 3279.

    Article  CAS  Google Scholar 

  18. Capriati, V.; Degennaro, L.; Florio, S.; Luisi, R. Tetrahedron Lett. 2001, 42, 9183.

    Article  CAS  Google Scholar 

  19. Gutierrez, D. A.; Lee, W.-C. C.; Shen, Y.; Li, J. J. Tetrahedron Lett. 2016, 57, 5372.

    Article  CAS  Google Scholar 

  20. Li, Z.; Ma, L.; Xu, J.; Kong, L.; Wu, X.; Yao, H. Chem. Commun. 2012, 48, 3763.

    Article  CAS  Google Scholar 

  21. Alla, S. K.; Sadhu, P.; Punniyamurthy, T. J. Org. Chem. 2014, 79, 7502.

    Article  CAS  PubMed  Google Scholar 

  22. Kamata, K; Agata, I.; Meyers, A. I. J. Org. Chem. 1998, 63, 3113.

    Article  CAS  Google Scholar 

  23. Huang, J.-M.; Zhang, J.-F.; Dong, Y.; Gong, W. J. Org. Chem. 2011, 76, 3511.

    Article  CAS  PubMed  Google Scholar 

  24. Shabsoug, B. M; Al-Shyoukh, A. Asian J. Chem. 2009, 21, 4954.

    CAS  Google Scholar 

  25. Arrieta, A.; Cossio, F. P.; Palomo, C. Tetrahedron 1985, 41, 1703.

    Article  CAS  Google Scholar 

  26. Fülöp, F; Pihlaja, K. Tetrahedron 1993, 49, 6701.

    Article  Google Scholar 

  27. Alva Astudillo, M. E.; Chokotho, N. C. J.; Jarvis, T. C.; Johnson, C. D.; Lewis, C. C.; McDonnell, P. D. Tetrahedron 1985, 41, 5919.

    Article  CAS  Google Scholar 

  28. Krivdin, L. B.; Larina, L. I.; Chernyshev, K. A.; Rulev, A. Y. Magn. Reson. Chem. 2006, 44, 178.

    Article  CAS  PubMed  Google Scholar 

  29. Wang, L.; Ma, Z.-G.; Wei, X.-J.; Meng, Q.-Y.; Yang, D.-T.; Du, S.-F.; Chen, Z.-F.; Wu, L.-Z.; Liu, Q. Green Chem. 2014, 16, 3752.

    Article  CAS  Google Scholar 

  30. Higashiyama, K.; Inoue, H.; Takahashi, H. Tetrahedron 1994, 50, 1083.

    Article  CAS  Google Scholar 

  31. Vilaivan, T.; Winotapan, C.; Banphavichit, V.; Shinada, T.; Ohfune, Y. J. Org. Chem. 2005, 70, 3464.

    Article  CAS  PubMed  Google Scholar 

  32. Dave, R. H.; Hosangadi, B. D. Tetrahedron 1999, 55, 11295.

    Article  CAS  Google Scholar 

  33. Matsuura, T.; Ito, Y. Tetrahedron Lett. 1973, 14, 2283.

    Article  Google Scholar 

  34. 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 

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

    Article  CAS  Google Scholar 

  36. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem. 2015, C71, 3.

    Google Scholar 

Download references

We thank the University of Bari Aldo Moro, the Polytechnic of Bari, the project Laboratorio SISTEMA (Code PONa300369) financed by Italian Ministry of Education, Universities, and Research.

We are also grateful to Chiara Claudio and Valeria Decaro for their precious contribution.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Claudia Carlucci or Renzo Luisi.

Additional information

Supplementary information file, containing NMR spectra, chiral HPLC data, and X-ray structural study parameters, is available at the journal website at http://link.springer.com/ journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 428–436

Electronic supplementary material

ESM 1

(PDF 2867 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Carlucci, C., Tota, A., Colella, M. et al. Use of Hypervalent Iodine in the Synthesis of Isomeric Dihydrooxazoles. Chem Heterocycl Comp 54, 428–436 (2018). https://doi.org/10.1007/s10593-018-2288-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-018-2288-9

Keywords

Navigation