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DOI: 10.1039/A804379E (Paper) Reference Section for: J. Chem. Res. (S), 1999, 128-129

Microwave-assisted Aminolysis of Epoxides Under Solvent-free Conditions Catalyzed by Montmorillonite Clay

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Mohammad M. Mojtahedi, Mohammad R. Saidi and Mohammad Bolourtchian

Abstract

The reaction of primary and secondary amines with epoxides in the presence of montmorillonite K10 clay, under solvent-free condtions and microwave irradiation affords high yields of β-amino alcohols.

References

  1. X. L. Fu and S. H. Wa, Synth. Commun., 1997, 27, 1677 CAS.
  2. A. J. Shuker, M. G. Siegel, D. P. Matthews and L. O. Weigel, Tetrahedron Lett., 1997, 38, 6149 CrossRef CAS.
  3. M. Chini, P. Crotti and F. Macchia, Tetrahedron Lett., 1990, 31, 4661 CrossRef.
  4. P. Van de Weghe and J. Collin, Tetrahedron Lett., 1995, 36, 1649 CrossRef CAS.
  5. J. Iqbal and A. Pandey, Tetrahedron Lett., 1990, 31, 575 CrossRef CAS.
  6. A. De, S. Ghosh and J. Igbal, Tetrahedron Lett., 1997, 38, 8379 CrossRef CAS.
  7. J. Auge and F. Leroy, Tetrahedron Lett., 1996, 37, 7715 CrossRef CAS.
  8. A. Vidal-Ferran, A. Moyano, M. A. Pericas and A. Riera, J. Org. Chem., 1997, 62, 4970 CrossRef CAS.
  9. M. Hori and K. D. Janda, J. Org. Chem., 1998, 63, 889 CrossRef.
  10. Y. Izumi, K. Urabe, M. Onaka, Zeolite, Clay and Heterpoly Acid in Organic Reaction, VCH, New York, 1992, pp. 21–47 Search PubMed.
  11. S. Caddick, Tetrahedron, 1995, 51, 10403 CrossRef.
  12. C. R. Strauss and R. W. Trainor, Aust. J. Chem., 1995, 48, 1665 CrossRef CAS.
  13. Selected Spectroscopic Data.—Compounds 3a–3g, 3j and 3k have been synthesized previously.3,4 The 1H NMR and 13C NMR spectra were recorded on a Bruker AC80 instrument using CDCl3 as solvent. Chemical shifts are in ppm relative to TMS. 3h: δH 1.28–1.51 (m, 4H), 1.98–2.52 (m, 6H), 3.01–3.18 (m, 2H), 3.42–3.63 (m, 1H), 3.63–3.90 (m, 3H), 4.70–5.12 (m, 2H), 5.34–5.88 (m, 1H). δC 23.46 (CH2), 54.34 (CH2), 59.18 (CH2), 67.94 (CH2), 72.24 (CH2), 72.94 (CH), 116.82 (CH2), 134.76 (CH). 3i: δH 2.12–2.75 (m, 6H), 3.31 (t, J= 5.8 Hz, 4H), 3.41–4.06 (m, 6H), 4.85–5.38 (m, 2H), 5.52–6.11 (m, 1H). δC 53.88 (CH2), 61.53 (CH2), 66.29 (CH2), 66.75 (CH2), 77.23 (CH2), 77.33 (CH), 116.88 (CH2), 134.69 (CH). 3l: δH 1.01 (d, J= 6.0 Hz, 6H), 1.61–1.88 (m, 4H), 2.27–2.76 (m, 6H), 3.34–3.98 (m, 3H), 4.51 (s, 1H). δC 21.92 (CH3), 23.99 (CH2), 54.20 (CH2), 59.10 (CH2), 68.10 (CH2), 70.91 (CH), 71.92 (CH). 3m: δH 1.20 (d, J= 6.1 Hz, 6H), 2.40–2.86 (m, 6H), 3.30–3.58 (m, 5H), 3.58–4.10 (m, 4H). δC 21.73 (CH3), 53.67 (CH2), 61.37 (CH2), 66.22 (CH2), 66.60 (CH2), 70.42 (CH), 71.75 (CH) Search PubMed.
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