A mild, convenient and efficient ring opening of oxiranes with aromatic amines was catalyzed by ammonium decatungstocerate (IV) in acetonitrile. The reaction afforded the corresponding products in 92–100% yields. The catalyst was reused for several times with consistent activity.
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(a) C. Bonini and G. Righi, Synthesis (1994) 225. (b) J.G. Smith, Synthesis (1984) 629
(a) D.J. Ager, I. Prakash and D. Schaad, Chem. Rev. 96 (1996) 835. (b) B.L. Chng and A. Ganesan, Bioorg. Med. Chem. Lett. 7 (1997) 1511. (c) G.A. Rogers, S.M. Parsons, D.C. Anderson, L.M. Nilsson, B.A. Bahr, W.D. Kornreich, R. Kaufman, R.S. Jacobs and B. Kirtman, J. Med. Chem. 32 (1989) 1217
(a) D. Roemer, H.H. Buescher, R.C. Hill, J. Pless, W. Bauer, F. Cardinaux, A. Closse, D. Hauser and R. Huguenin, Nature 238 (1977) 547. (b) C. Auvin-Guette, S. Rebuffat, Y. Prigent and B. Bodo, J. Am. Chem. Soc. 114 (1992) 2170
S. Wu R. Takeya M. Eto C. Tomizawa (1987) J. Pestic. Sci. 12 221
(a) S. Masamune and R.P. Short, J. Am. Chem. Soc. 111 (1989) 1892. (b) H.C. Brown, U.S. Racherla and P.J. Pellechia, J. Org. Chem. 55 (1990) 1868. (c) R. Berenguer, J. Garcia and J. Vilarrasa, Tetrahedron Asymmetr. 5 (1994) 165. (d) J. Takehara, S. Hashiguchi, A. Fujii, S.I. Inoue, T. Ikaria and R. Noyori, Chem. Commun. (1996) 233
(a) M. Mousseron, J. Jullien and Y. Jolchine, Bull. Chem. Soc. Jpn. (1952) 757. (b) J.A. Deyrub and C.L. Moyer, J. Org. Chem. 34 (1969) 175
(a) J. Iqbal and A. Pandey, Tetrahedron Lett. 31 (1990) 575. (b) S. Sagava, H. Abe, Y. Hase and T. Inaba, J. Org. Chem. 64 (1999) 4962. (c) P. Van de Weghe and J. Collin, Tetrahedron Lett. 36 (1995) 1649. (d) J. Yamada, Y. Yumoto and Y. Yamamoto, Tetrahedron Lett. 30 (1989) 4255. (e) X.-L. Fu and S.-H. Wu, Synth. Commun. 27 (1997) 1677. (f) G. Sekar and V.K. Sing, J. Org. Chem. 64 (1999) 267. (g) S. Sagava, H. Abe, Y. Hase and T. Inaba, J. Org. Chem. 64 (1999) 4962. (h) M. Meguro, N. Asao and Y.J. Yamamoto, J. Chem. Soc., Perkin Trans. 1 (1994) 2597. (i) M. Chini, P. Crotti, L. Favero, F. Macchina and M. Pineschi, Tetrahedron Lett. 35 (1994) 433. (j) M. Fujiwara, M. Imada, A. Baba and H. Matsuda, Tetrahedron Lett. 30 (1989) 739. (k) L.R. Reddy, M.A. Reddy, N. Bhanumathi and K.R. Rao, Synlett. (2000) 339. (l) L.R. Reddy, M.A. Reddy, N. Bhanumathi and K.R. Rao, Synlett. (2001) 831
V. Mirkhani S. Tangestaninejad B. Yadollahi L. Alipanah (2003) Tetrahedron 59 8213
(a) I.V. Kozhevnikov, Chem. Rev. 98 (1998) 171. (b) N. Mizuno and M. Misono, J. Mol. Catal. 64 (1990) 1. (c) Y. Ono, in: Perspective in Catalysis, (eds.), J.M. Thomas and K.I. Zamaraev (Blackwell, London, 1992), p. 431. (d) I.V. Kozhevnikov, Catal. Rev. Sci. Eng. 37 (1995) 311. (e) M. Misono, Catal. Rev. Sci. Eng. 29 (1987) 269; 30 (1988) 339. (f) N. Mizuno and M. Misono, Chem. Rev. 98 (1998) 199. (g) N. Nojori and M. Misono, Appl. Catal. 95 (1993) 559. (h) Y. Izumi, K. Urabe and M. Onaka, Zeolite, Clay and Heteropoly Acid in Organic Reactions, (Kodansha/VCH, Tokyo, 1992), p. 99. (i) T. Okuhara, N. Mizuno and M. Misono, Adv. Catal. 41 (1996) 113. (j) C.L. Hill and C.M. Prosser-McCartha, Coord. Chem. Rev., 143 (1995) 407
(a) R.D. Peacock and T.J.R. Weakley, J. Chem. Soc. A (1971) 1836. (b) R. Shiozaki, H. Goto and Y. Kera, Bull. Chem. Soc. Jpn. 66 (1993) 2790
(a) G.H. Posner, Angew. Chem. Int. Ed. Engl. 17 (1978) 487. (b) D.C. Bailey and S.H. Langer, Chem. Rev. 81 (1981) 109. (c) P. Laszol, Acc. Chem. Res. 19 (1986) 121
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Mirkhani, V., Tangestaninejad, S., Yadollahi, B. et al. Ammonium decatungstocerate (IV): an efficient catalyst for ring opening of epoxides with aromatic amines. Catal Lett 101, 93–97 (2005). https://doi.org/10.1007/s10562-004-3755-8
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DOI: https://doi.org/10.1007/s10562-004-3755-8