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Microwave-assisted Michael addition of sulfonamides to α,β-unsaturated esters: A rapid entry to protected β-amino acid synthesis

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Abstract

An efficient, clean and very simple procedure for the synthesis of protected β-amino acids is described. Michael addition of sulfonamides to α,β-unsaturated esters in the presence of K2CO3 and tetrabutylammonium bromide (TBAB) under microwave irradiation affords the title compounds in good to high yields and short reaction times. This new method affords protected β-amino acids in high yields and short reaction times.

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References

  1. A.R. Khosropour, K. Esmaeilpoor, A. Moradie, J. Iran. Chem. Soc. 3 (2006) 81

    Article  CAS  Google Scholar 

  2. M. Mamaghani, K. Tabatabaeian, M. Mirzaeinejad, M. Nikpassand, J. Iran. Chem. Soc. 3 (2006) 89

    Article  CAS  Google Scholar 

  3. K.G. Desai, J.P. Raval, K.R. Desai, J. Iran. Chem. Soc. 3 (2006) 233

    CAS  Google Scholar 

  4. S. Balalaie, M. Soleiman,- Beigi, F. Rominger, J. Iran. Chem. Soc. 2 (2005) 319

    Article  CAS  Google Scholar 

  5. H. Loghmani-Khouzani, M.M. Sadeghi, R. Ranjbar-Karimi, J. Iran. Chem. Soc. 2 (2005) 330

    Article  CAS  Google Scholar 

  6. K. Tanaka, Solvent-free Organic Synthesis, Wiley-VCH, GmbH and KGaA, Weinheim, 2004

    Google Scholar 

  7. A. Loupy, Microwave in Organic Synthesis, Wiley-VCH, Weinheim, 2004

    Google Scholar 

  8. R.S. Varma, Advances in Green Chemistry: Chemical Synthesis Using Microwave Irradiation, Astra Zeneca Research Foundation, Kavitha Printers, Bangalore, India, 2002

    Google Scholar 

  9. B.L. Hayes, Microwave Synthesis, Chemistry at the Speed of Light, CEM Publishing, Mathews, NC, 2002

    Google Scholar 

  10. H.M. Kingston, S.J. Haswell, Microwave-Enhanced Chemistry, Fundamentasls, Sample Preparation, and Applications, American Chemical Society, Washington, D.C. (1997)

    Google Scholar 

  11. V.K. Ahluwalia, R. Aggarwal, Organic Synthesis, Special Techniques, Alpha Science International Ltd., Pangbourne, UK, 2001.

    Google Scholar 

  12. G.H. Imanzadeh, A. Khalafi-Nezhad, A. Zare, A. Hasaninejad, A.R. Moosavi Zare, A. Parhami, J. Iran. Chem. Soc. 4 (2007) 229

    Article  CAS  Google Scholar 

  13. A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, G.R. Nejabat, J. Iran. Chem. Soc. 4 (2007) 271

    Google Scholar 

  14. A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi Zare, A. Parhami, G.R. Nejabat, Arkivoc i (2007) 58

  15. A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, G.R. Nejabat, Synth. Commun. 36 (2006) 3549

    CAS  Google Scholar 

  16. A. Khalafi-Nezhad, A. Zare, A. Parhami, M.N. Soltani Rad, G.R. Nejabat, Can. J. Chem. 84 (2006) 979

    CAS  Google Scholar 

  17. A. Khalafi-Nezhad, A. Zare, M.N. Soltani Rad, B. Mokhtari, A. Parhami, Synthesis (2005) 419

  18. A. Khalafi-Nezhad, M.N. Soltani Rad, A. Khoshnood, Synthesis (2004) 583

  19. A. Khalafi-Nezhad, M.N. Soltani Rad, G.H. Hakimelahi, Helv. Chim. Acta 86 (2003) 2396

    CAS  Google Scholar 

  20. A. Khalafi-Nezhad, F. Alamdari, N. Zekri, Tetrahedron 56 (2000) 7503

    CAS  Google Scholar 

  21. A. Khalafi-Nezhad, A. Hashemi, Iran. J. Chem. Chem. Eng. 20 (2001) 9; Chem. Abstr. 137 (2002) 232608

    CAS  Google Scholar 

  22. A. Khalafi-Nezhad, B. Mokhtari, M.N. Soltani Rad, Tetrahedron Lett. 44 (2003) 7325

    CAS  Google Scholar 

  23. A. Khalafi-Nezhad, A. Hashemi, J. Chem. Res., Synop. (1999) 720.

  24. S.H. Gellman, Acc. Chem. Res. 31 (1998) 173

    CAS  Google Scholar 

  25. M. Windholz, S. Budavari, L.Y. Stroumtsos, M.N. Fertig, The Merck Index, An Encyclopedia of Chemicals and Drugs, 9th ed., Merck, Rahway, NJ, 1976

    Google Scholar 

  26. S. Shinagawa, T. Kanamaru, S. Harada, M. Asai, H. Okazaki, J. Med. Chem. 30 (1987) 1458

    CAS  Google Scholar 

  27. C. Shih, L.S. Gossett, J.M. Gruber, C.S. Grossman, S.L. Andis, R.M. Schultz, J.F. Worzalla, T.H. Corbett, J.T. Metz, Bioorg. Med. Chem. Lett. 9 (1999) 69

    CAS  Google Scholar 

  28. C. Yuan, R.M. Williams, J. Am. Chem. Soc. 119 (1997) 11777.

    CAS  Google Scholar 

  29. A. Dobrev, C. Ivanov, C.R. Hebd. Seances Acad. Sci. 306 (1988) 523

    CAS  Google Scholar 

  30. H. Nohira, K. Watanabe, T. Ishikawa, K. Saigo, Heterocycles (1977) 301

  31. J. Pigulla, E. Roeder, Liebigs. Ann. Chem. (1978) 390.

  32. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A. 252 (2006) 150

    CAS  Google Scholar 

  33. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Chem. Commun. (2005) 789

  34. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Cat. 347 (2005) 655

    CAS  Google Scholar 

  35. B. Tamami, A. Fadavi, M. Tamami, Iran. Polym. J. 15 (2006) 799

    CAS  Google Scholar 

  36. N. Azizi, M.R. Saidi, Tetrahedron 60 (2004) 383

    CAS  Google Scholar 

  37. I. Reboule, R. Gil, J. Collin, Tetrahedron Lett. 46 (2005) 7761

    CAS  Google Scholar 

  38. N.S. Shaikh, V.H. Deshpande, A.V. Bedekar, Tetrahedron 57 (2001) 9045

    CAS  Google Scholar 

  39. K. Surendra, N.S. Krishnaveni, R. Sridhar, K.R. Rao, Tetrahedron Lett.47 (2006) 2125

    CAS  Google Scholar 

  40. M.K.Chaudhuri, S. Hussain, M.L. Kantam, B. Neelima, Tetrahedron Lett.46 (2005) 8329.

    CAS  Google Scholar 

  41. M. Maggini, M. Prato, M. Ranelli, G. Scorrano, Tetrahedron Lett. 33 (1992) 6537

    CAS  Google Scholar 

  42. T. Wakabayashi, M. Saito, Tetrahedron Lett.38 (1977) 93

    Google Scholar 

  43. K.H. Ann, S.J. Lee, Tetrahedron Lett. 35 (1994) 1875.

    Google Scholar 

  44. O.A. Moe, D.T. Warner, J. Am. Chem. Soc. 71 (1949) 1251

    CAS  Google Scholar 

  45. G. Cardillo, A.D. Simone, L. Gentilucci, P. Sabatino, C. Tomasini, Tetrahedron Lett.35 (1994) 5051.

    Google Scholar 

  46. A. Reitz, M. Verlander, M. Goodman, Tetrahedron Lett. 23 (1982) 751.

    CAS  Google Scholar 

  47. M. Hosseini Sarvari, H. Sharghi, Tetrahedron 61 (2005) 10903

    Google Scholar 

  48. F. Tamaddon, M.A. Amrollahi, L. Sharafat, Tetrahedron Lett. 46 (2005) 7841.

    CAS  Google Scholar 

  49. P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2002

    Book  Google Scholar 

  50. M.M. Khodaei, A.R. Khosropour, S. Ghaderi, J. Iran. Chem. Soc. 3 (2006) 69

    Article  CAS  Google Scholar 

  51. M.M. Mojtahedi, M.S. Abaee, H. Abbasi, J. Iran. Chem. Soc. 3 (2006) 93.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Basic Sciences, Mohagheghe Ardebili University, Ardebil, 179, Iran

    G. H. Imanzadeh & A. R. Moosavi Zare

  2. Department of Chemistry, Payame Nour University of Bushehr, Bushehr, 1698, Iran

    A. Zare

  3. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    A. Khalafi-Nezhad & A. Parhami

  4. Department of Chemistry, Faculty of Sciences, Persian Gulf University, Bushehr, 75169, Iran

    A. Hasaninejad

Authors
  1. G. H. Imanzadeh
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  2. A. Zare
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  3. A. Khalafi-Nezhad
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  4. A. Hasaninejad
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  5. A. R. Moosavi Zare
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  6. A. Parhami
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Corresponding authors

Correspondence to A. Zare or A. Khalafi-Nezhad.

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Imanzadeh, G.H., Zare, A., Khalafi-Nezhad, A. et al. Microwave-assisted Michael addition of sulfonamides to α,β-unsaturated esters: A rapid entry to protected β-amino acid synthesis. JICS 4, 467–475 (2007). https://doi.org/10.1007/BF03247234

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  • DOI: https://doi.org/10.1007/BF03247234

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