Free accessResearch articleFirst published online 2003-6
Intermolecular Reductive Coupling Cyclisation of 1,1-Diaryl-2,2-Dicyanoethylenes with Aldehydes or Ketones to Synthesise Polysubstituted 2,3-Dihydrofurans and Cyclopentenylamines Promoted by Samarium Metal in DMF
The intermolecular reductive coupling and cyclisation of 1,1-diaryl-2,2-dicyanoethylenes with carbonyl compounds promoted by metallic samarium in DMF afforded functionalised 2,3-dihydrofurans and cyclopentenylamines.
(a) GirardP., NamyJ. L., and KaganH. B., J. Am. Chem. Soc., 1980, 102, 2693; (b) A. Krief and A. M. Laval, Chem Rev., 1999, 99, 745; (c) G. A. Molander, Acc. Chem. Res., 1998, 31, 603; (d) G. A. Molander and C. R. Harris, Tetrahedron, 1998, 54, 3321; (e) G. A. Molander, Harris C. R., Chem Rev., 1996, 96, 307; (f) T. Imamota, Lanthanides in Organic Synthesis, Academic Press: London, 1994, Chap. 4; (g) G. A. Molander, Chem Rev., 1992, 92, 29; (h) D. P. Curran, T. L. Fevig, C. P. Jasperse and M. J. Totleben, Synlett, 1992, 943.
2.
BanikB.K., Eur. J. Org. Chem., 2002, 2431.
3.
(a) OgawaA., NankeT., TakamiN., SuminoY., RyuI., and SonodaN., Chem. Lett., 1994, 379; (b) G. A. Molander and J. B. Etter, J. Org. Chem., 1986, 51, 1778; (c) T. Imamoto, T. Takeyama and H. Koto, Tetrahedron Lett., 1986, 27, 3243; (d) R. Yanada, N. Negoro, M. Okaniwa, Y. Miwa, T. Taga, K. Yanada and T. Fujita, Synlett, 1999, 537; (e) A. Ogawa, N. Takami, M. Sekiguchi, I. Ryu, N. Kambe and N. Sonoda, J. Am. Chem. Soc., 1992, 114, 8729; (f) G. A. Molander and J. B. Etter, J. Org. Chem., 1987, 52, 3942.
4.
(a) WangL., and ZhangY., Tetrahedron, 1998, 54, 11129; (b) B. K. Banik, C. Mukhopadhyay, M. S. Venkatraman and F. F. Becker, Tetrahedron Lett., 1998, 39, 7243; (c) R. Yanada, N. Negora and K. Yanada, Fujita, T. Tetrahedron Lett., 1997, 38, 3271; (d) R. Yanata, K. Bessho and K. Yanada, Chem. Lett., 1994, 1279; (e) Y. Komachi and T. Kudo, Chem. Pharm. Bull., 1994, 42, 402; (f) Y. Komachi and T. Kudo, Chem. Pharm. Bull., 1995, 43, 1422; (g) A. Ghatak, F. F. Becker and B. K. Banik, Tetrahedron Lett., 2000, 41, 3793; (h) S. Talukdar and J.-M. Fang, J. Org. Chem., 2001, 66, 330.
5.
(a) YacovanA., and HozS., J. Org. Chem., 1997, 62, 771; (b) A. Yacovan, S. Hoz and I. Bilkis J. Am. Chem. Soc., 1996, 118, 261.
6.
(a) RapoportZ., Isr. J. Chem., 1970, 8, 749; (b) J. L. Namy, J. Souppe and H. B. Kagan, Tetrahedron Lett., 1983, 24, 765.
7.
XuX.L., and ZhangY. M., J. Chem. Soc. Perkin. Trans. 1, 2001, 2836
8.
ZhouL.H., ZhangY. M., and ShiD. Q., Tetrahedron Lett., 1998, 39, 8491.
9.
(a) DeanF.M., and SargentM. V., in Comprehensive Heterocyclic Chemistry, ed. BirdC. W.; CheesemanG. W.Pergamon Press, New York, 1984, vol. 4, part 3, p. 531; (b) F. M. Dean, in Advances in Heterocyclic Chemistry, ed. Katritzky, A. R. Academic Press, New York, 1982, vol. 30, p. 167; vol. 31, p. 237; (c) K. B. Becker, Tetrahedron, 1980, 36, 1717; (d) G. G. Melibyan, A. B. Sargsyan, D. A. Mkrtchyan, G. Kh. Azaryan and Sh. O. Badanyan, Khim. Geterotsikl. Soedin., 1992, 4, 468.
10.
(a) MarshallJ.A., and SehonC. A., J. Org. Chem., 1995, 60, 5966; (b) Y. Himeda, M. Hatanaka and I. Ueda, J. Chem. Soc. Chem. Commun., 1995, 449; (c) M. S. Baird, A. G. W. Baxter, A. Hoorfar and I. Jefferies, J. Chem. Soc. Perkin Trans. 1, 1991, 2575; (d) J. C. Caesar, D. V. Griffiths, P. A. Griffiths and J. C. Tebby, J. Chem. Soc. Perkin Trans. 1., 1989, 2425; (e) I. F. Wilson and J. C. Tebby, J. Chem. Soc. Perkin Trans. 1, 1972, 2830; (f) E. Zbiral, Synthesis, 1974, 775; (g) F. M. Dean, Adv. Heterocycl. Chem., 1982, 30, 167; (h) E. E. Schweizer, A. T. Wehman and D. M. Nycz, J. Org. Chem., 1973, 38, 1583; (i) E. E. Schweizer and J. G. Liehr, J. Org. Chem., 1968, 33, 583; (j) R. Burgada and R. Setton, The Chemistry of Organophosphorus Compounds, Patai, S.; Hartley, F.R. Eds, Wiley, 1994, vol. 3, p 231.
11.
(a) ZhouL.H., and ZhangY. M., Tetrahedron Lett., 1997, 38, 8063; (b) H. B. Kagan, P. Griard and J. L. Namy, Tetrahedron, 1981, 37 (Suppl 1), 175.
12.
CookA.G., Enamines: Their Synthesis, Structure and Reaction, Marcel Dekker, New York, 1969.
13.
(a) StorkG., BrizzolaraA., LandesmanH., SzmuszkoviczJ., and TerrellR., J. Am. Chem. Soc., 1963, 85, 207; (b) H. O. House, Modern Synthetic Reaction, 2nd ed, (W, Benjamin, California, 1972), p 742.
14.
(a) SchaeferJ.P., and BloomfieldJ. J., Organic Reactions, 1967, 15, 1; (b) G. Seitz and H. Monnighoff, Tetrahedron Lett., 1971, 12, 4889; (c) R. Helmers and W. Kaiser, Tetrahedron Lett., 1971, 12, 3853; (d) S. Wawzonek, A. R. Zigman and G. R. Hansen, J. Electrochem. Soc., 1970, 117, 1351.
15.
(a) BaronH., RemfryF. G. P., and ThorpeJ. F., J. Chem. Soc., 1904, 85, 1726; (b) K. Ziegler, E. Eberle and M. Ohlinger, Ann, 1933, 504, 94.
16.
YuY.P., LinR. H., and ZhangY. M., Tetrahedron Lett., 1993, 34, 4547.