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Synthesis of chiral α-carbonyl-δ-nitro-ketenedithioacetals via l-proline-catalyzed Michael addition reaction

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Abstract

Regioselective synthesis of 1,1-bis(methylthio)-6-nitro-5-arylhex-1-en-3-one has been achieved from α-alkenoylketene dithioacetals with nitromethane using l-proline catalyst via Michael addition. The synthesized compounds 3a–j were well characterised by NMR and mass spectral techniques. One of the structures was confirmed by single crystal XRD. The enantioselectivity and its specific rotation of synthesized compounds were analyzed. All the compounds were screened for their anti-oxidant property, most of the compounds having the ability to scavenge free radicals.

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References

  1. A. Thuiller, J. Vialle, Bull. Soc. Chim. Fr. 2182–2187 (1962)

  2. B. Myrboh, C.V. Ashokan, H. Ila, H. Junjappa, Synthesis 1, 50–51 (1984)

    Article  Google Scholar 

  3. H. Junjappa, H. Ila, C.V. Ashokan, Tetrahedron 46, 5423–5506 (1990)

    Article  CAS  Google Scholar 

  4. R.K. Dieter, Tetrahedron 42, 3029–3096 (1986)

    Article  CAS  Google Scholar 

  5. L. Pan, B. Bi, Q. Liu, Chem. Soc. Rev. 42, 1251–1286 (2013)

    Article  CAS  Google Scholar 

  6. L. Zhang, X. Xu, J. Tan, L. Pand, W. Xia, Q. Liu, Chem. Commun. 46, 3357–3359 (2010)

    Article  CAS  Google Scholar 

  7. Y. Li, X. Xu, J. Tan, C. Xia, D. Zhang, Q. Liu, J. Am. Chem. Soc. 133, 1775–1777 (2011)

    Article  CAS  Google Scholar 

  8. M. Yamaguchi, T. Shiraishi, Y. Igarashi, M. Hirama, Tetrahedron Lett. 35, 8233–8236 (1994)

    Article  CAS  Google Scholar 

  9. B. Vakulya, S. Varga, A. Csampai, T. Soos, Org. Lett. 7, 1967–1969 (2005)

    Article  CAS  Google Scholar 

  10. H. Gotoh, H. Ishikawa, Y. Hayashi, Org. Lett. 9, 5307–5309 (2007)

    Article  CAS  Google Scholar 

  11. X. Bi, D. Dong, Q. Liu, Q. Pan, L. Zhao, B. Li, J. Am. Chem. Soc. 127, 4578–4579 (2005)

    Article  CAS  Google Scholar 

  12. Y. Ma, M. Wang, D. Li, B. Bekturhun, J. Liu, Q. Liu, J. Org. Chem. 74, 3116–3121 (2009)

    Article  CAS  Google Scholar 

  13. J. Tan, X. Xu, Y. Li, Q. Liu, Angew. Chem. Int. Ed. 48, 2868–2872 (2009)

    Article  CAS  Google Scholar 

  14. L. Zhang, F. Liang, X. Cheng, Q. Liu, J. Org. Chem. 74, 899–902 (2009)

    Article  CAS  Google Scholar 

  15. L. Zhao, F. Liang, X. Bi, S. Sun, Q. Liu, J. Org. Chem. 71, 1094–1098 (2006)

    Article  CAS  Google Scholar 

  16. H. Wang, Y.L. Zhao, C.Q. Ren, A. Diallo, Q. Liu, Chem. Commun. 47, 12316–12318 (2011)

    Article  CAS  Google Scholar 

  17. Z. Fu, M. Wang, Y. Dong, Q. Liu, J. Org. Chem. 74, 6105–6110 (2009)

    Article  CAS  Google Scholar 

  18. X. Bi, D. Dong, Y. Li, Q. Liu, Q. Zhang, J. Org. Chem. 70, 10886–10889 (2005)

    Article  CAS  Google Scholar 

  19. CCDC 1484113 contains the crystallographic data for this paper as supplementary information. This information shall be obtained from The Cambridge Crystallographic Data Centre

  20. A. Rani, S. Jain, P. Dureja, R. Kumar, A. Kumar, Indian J. Chem. 50B, 1524–1531 (2011)

    CAS  Google Scholar 

  21. B.P. Bandgar, S.A. Patil, R.N. Gacche, B.L. Korbad, B.S. Hote, S.N. Kinkar, S.S. Jalde, Biorg. Med. Chem. Lett. 20, 730–733 (2010)

    Article  CAS  Google Scholar 

  22. T.C. Shekar, G. Anju, Am. J. Ethnomed. 1, 244–249 (2014)

    Google Scholar 

  23. G.O. Adegoke, A.G. GopalaKrishna, J. Am. Oil Chem. Soc. 75, 1047–1052 (1998)

    CAS  Google Scholar 

  24. H. Ye, C. Zhou, Y. Sun, X. Zhang, J. Liu, Q. Hu, X. Zeng, Eur. J. Food Res. Technol. 230, 101–109 (2009)

    Article  CAS  Google Scholar 

  25. K. Girija, A. Hemalatha, C. Saranya, C. Parthiban, P. Anantharaman, Int. J. Bioassays 02, 1185–1189 (2013)

    Google Scholar 

  26. P. Molyneux, Songklanakarin J. Sci. Tech. 2, 211–219 (2004)

    Google Scholar 

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Acknowledgements

The author thank UGC-MRP and DST-MRP, New Delhi, India, for financial assistance. We thank DST-IRPHA for funding towards high-resolution NMR spectroscopy. The author, AD, thanks Mr. D. Maheshwaran, School of Chemistry, Madurai Kamaraj University, Madurai, for his generous help in solving crystal data and also thanks Dr. Shakila Mohan, School of Biotechnology, Madurai Kamaraj University, for her benevolent help in acquiring the absorbance for the DPPH assay.

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Authors and Affiliations

  1. Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai, Tamil Nadu, 625 021, India

    Mathiyazhagan Arun Divakar & Sivakumar Shanmugam

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  1. Mathiyazhagan Arun Divakar
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  2. Sivakumar Shanmugam
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Correspondence to Sivakumar Shanmugam.

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Arun Divakar, M., Shanmugam, S. Synthesis of chiral α-carbonyl-δ-nitro-ketenedithioacetals via l-proline-catalyzed Michael addition reaction. Res Chem Intermed 43, 6863–6873 (2017). https://doi.org/10.1007/s11164-017-3025-1

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