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Theoretical study of the regioselectivity of the Huisgen reaction

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Abstract

From the structure of a series of spiro (pyrrolidine-2,3′-oxindole) derivatives synthesized by Huisgen reaction of isatin, α-amino acids, and different olefins, different regioselectivities were found. The possible mechanism of the Huisgen reaction of oxindole azomethine ylide and the substituent of olefins was investigated using a B3LYP/6-311G* level of theory, and the results show that the regioselection depends on the energy barrier between the stacking state and the regioisomer. This mechanism can also be applied to the illumination of other Huisgen reactions.

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References

  1. R. Huisgen, Angew. Chem. Int. Ed. 2, 633 (1963)

    Article  Google Scholar 

  2. S. Rehn, J. Bergman, B. Stensland, Eur. J. Org. Chem. 413 (2004)

  3. S. Abdel-Aziz, El-Ahl, Heteroatom Chem. 13, 324 (2002)

    Article  Google Scholar 

  4. D. Fokas, W.J. Rvan, D.S. Casebier, D.L. Coffen, Tetrahedron Lett. 39, 2235 (1998)

    Article  CAS  Google Scholar 

  5. R.S. Manian, J. Jayashankaran, S.S. Kumar, R. Raghunathan, Tetrahedron Lett. 47, 829 (2006)

    Article  CAS  Google Scholar 

  6. R.A. Amal, R. Raghunathan, M.R. SrideviKumari, N. Raman, Bioorg. Med. Chem. 11, 407 (2003)

    Article  Google Scholar 

  7. G. Chen, H.P. He, J. Ding, X.J. Hao, Heterocyl. Commun. 15(5), 355 (2009)

    CAS  Google Scholar 

  8. G. Chen, Y. Wu, X.F. Gu, Heterocyl. Commun. 17(3–4), 161 (2011)

    Google Scholar 

  9. G. Chen, J. Zhang, Y. Wu, Res. Chem. Intermediat. 38, 413 (2012)

    Article  CAS  Google Scholar 

  10. G. Chen, J. Yang, S. Gao, H.P. He, S.L. Li, Y.T. Di, Y. Chang, Y. Lu, X.J. Hao, Mol. Diver. 16(1), 151 (2012)

    Article  Google Scholar 

  11. M.J. Kornet, A.P. Thio, J. Monatsh. Chem. 19, 892 (1976)

    CAS  Google Scholar 

  12. M. Oimomi, M. Hamada, T.J. Hara, Antibiotics 27, 987 (1975)

    Google Scholar 

  13. H. Pajouhesh, R. Parsons, F.D. Popp, J. Pharm. Sci. 72, 318 (1983)

    Article  CAS  Google Scholar 

  14. F.D. Popp, J. Heter. Chem. 21, 1367 (1984)

    Article  Google Scholar 

  15. J.W. Skiles, D. MeNeil, Tetrahedron Lett. 31, 7277 (1990)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the grants from Chinese Ministry of Science and Technology (2009CB522303), Important Science & Technology Specific Projects of Innovative Program of Shaanxi Province (2010ZDKG-46), Scientific and Technological Plan Projects of Shaanxi Province of China (2012KJXX-40) and Scientific Research Program Funded by Shaanxi Provincial Education Department (12JK0582, 12JK0589).

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Authors and Affiliations

  1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, People’s Republic of China

    Gang Chen, Jing Yang, Suo Gao, Yu Zhang & Xiao-jiang Hao

  2. College of Chemistry and Chemical Engineering, Xi’an Shiyou University, Xi’an, Shaanxi, 710065, China

    Gang Chen

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  1. Gang Chen
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  2. Jing Yang
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  3. Suo Gao
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  4. Yu Zhang
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  5. Xiao-jiang Hao
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Correspondence to Xiao-jiang Hao.

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Chen, G., Yang, J., Gao, S. et al. Theoretical study of the regioselectivity of the Huisgen reaction. Res Chem Intermed 39, 1245–1250 (2013). https://doi.org/10.1007/s11164-012-0680-0

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  • DOI: https://doi.org/10.1007/s11164-012-0680-0

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