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BF3·SiO2 is a simple and efficient Lewis acid catalyst for the one-pot synthesis of polyfunctionalized piperidin-4-ones

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Abstract

A range of Lewis acid catalysts were used for a series of one-pot multi-component reactions. Of them, silica-supported boron trifluoride (BF3·SiO2) was found to be an effective catalyst for the promotion of the modified Mannich condensation of ketones, aldehydes, and ammonium acetate in 1:2:1 molar ratio to afford 3,5-dialkyl-2,6-diarylpiperidin-4-ones in high yields of 80–92%. Also this simple, easily prepared, and reusable catalyst executed the condensation very effectively in a significantly shorter reaction duration (about 1–4 h) than the conventional method, which requires 1 day or more and involves a tedious work-up procedure. Further, this protocol ensures the stereospecificity; accordingly, all the synthesized piperidones adopted a chair conformation with an equatorial orientation of all substituents at C-2, C-3, C-5, and C-6.

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References

  1. Parthiban P, Aridoss G, Rathika P, Ramkumar V, Kabilan S (2009) Bioorg Med Chem Lett 19:2981

    Article  CAS  Google Scholar 

  2. Parthiban P, Balasubramanian S, Aridoss G, Kabilan S (2005) Med Chem Res 14:523

    Article  CAS  Google Scholar 

  3. Aridoss G, Parthiban P, Ramachandran R, Prakash M, Kabilan S, Jeong YT (2009) Eur J Med Chem 44:577

    Article  CAS  Google Scholar 

  4. Rani M, Parthiban P, Ramachandran R, Kabilan S (2011) Med Chem Res. doi:10.1007/s00044-011-9573-9

  5. El-Subbagh HI, Abu-Zaid SM, Mahran MA, Badria FA, Alobaid AM (2000) J Med Chem 28:2915

    Article  Google Scholar 

  6. Ganellin CR, Spickett RGW (1965) J Med Chem 8:619

    Article  CAS  Google Scholar 

  7. Lijinsky W, Taylor HW (1975) Int J Cancer 16:318

    Article  CAS  Google Scholar 

  8. Baliah V, Jeyaraman R, Chandrasekaran L (1983) Chem Rev 83:379

    Article  CAS  Google Scholar 

  9. Katritzky AR, Fan WJ (1990) J Org Chem 55:3205

    Article  CAS  Google Scholar 

  10. Takahata H, Ouchi H, Ichionose M, Nemoto H (2002) Org Lett 4:3459

    Article  CAS  Google Scholar 

  11. Honda T, Kimura M (2000) Org Lett 2:3925

    Article  CAS  Google Scholar 

  12. Balme G, Bossharth E, Monteiro N (2003) Eur J Org Chem 4101

  13. Wangelin J, Von A, Neumann H, Gordes D, Klaus S, Strubing D, Beller M (2003) Chem Eur J 9:4286

    Article  Google Scholar 

  14. Eilbracht P, Baerfacker L, Buss C, Hollmann C, Kitsos-Rzychon BE, Kranemann CL, Rische T, Roggenbuck R, Schmidt A (1999) Chem Rev 99:3329

    Article  CAS  Google Scholar 

  15. Bora U, Saikia A, Boruah RC (2003) Org Lett 5:435

    Article  CAS  Google Scholar 

  16. Noller CR, Baliah V (1948) J Am Chem Soc 70:3853

    Article  CAS  Google Scholar 

  17. Cramer N, Juretschke J, Laschat S, Baro A, Frey W (2004) Eur J Org Chem 1397

  18. Xu Q, Yang Z, Yin D, Wang J (2006) Front Chem Eng China 3:201

    Article  Google Scholar 

  19. Wang M, Song Z-G, Wan X, Zhao S (2009) Monatsh Chem 140:1205

    Article  CAS  Google Scholar 

  20. Bigdeli MA, Nemati F, Mahdavinia GH (2007) Tetrahedron Lett 48:6801

    Article  CAS  Google Scholar 

  21. Yadav JS, Reddy BVS, Shankar KS, Premalatha K, Swamy T (2008) Lett Org Chem 5:353

    Article  CAS  Google Scholar 

  22. Srinivasan M, Perumal S, Selvaraj S (2005) ARKIVOC xi:201

  23. Dindulkar SD, Parthiban P, Puranik VG, Jeong YT (2011) J Mol Struct 990:44

    Article  CAS  Google Scholar 

  24. Klapotke TM, McMonagle F, Spence RR, Winfield JM (2006) J Fluorine Chem 127:1446

    Article  Google Scholar 

  25. Vatsadze SZ, Karinova Yu V, Kovalkina MA, Zyk NV (2000) Chem Heterocycl Comp 36:1185

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This research work was supported by the Industrial Technology Development Program, which was conducted by the Ministry of Knowledge Economy of the Korean Government.

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Authors and Affiliations

  1. Department of Image Science and Engineering, Pukyong National University, Busan, 608-737, Korea

    Someshwar D. Dindulkar & Yeon Tae Jeong

  2. Department of Biomedicinal Chemistry, Inje University, Gyeongnam, Gimhae, 621-749, Korea

    Paramasivam Parthiban

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  1. Someshwar D. Dindulkar
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  2. Paramasivam Parthiban
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  3. Yeon Tae Jeong
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Correspondence to Yeon Tae Jeong.

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Dindulkar, S.D., Parthiban, P. & Jeong, Y.T. BF3·SiO2 is a simple and efficient Lewis acid catalyst for the one-pot synthesis of polyfunctionalized piperidin-4-ones. Monatsh Chem 143, 113–118 (2012). https://doi.org/10.1007/s00706-011-0576-5

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  • DOI: https://doi.org/10.1007/s00706-011-0576-5

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