Facile synthesis of polysubstituted 2,3-dihydrofuran and cyclopentenylamine derivatives promoted by samarium diiodide

Synthetic Communications

Volumn 33, Issue 15, 2003, Pages 2643-2656

  Xu, Xiaoliang ^a   Zhang, Yongmin ^a,b  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINO 2 ETHOXYCARBONYL 3,3 DIPHENYL 4 (3 BROMOPHENYL) 5 BENZOYLCYCLOPENTENE; 1 AMINO 2 ETHOXYCARBONYL 3,3 DIPHENYL 4 (4 METHYLPHENYL) 5 BENZOYLCYCLOPENTENE; 2 AMINO 1 CYANO 3 (4 BROMOBENZOYL) 4 (4 METHYLPHENYL) 5,5 DIPHENYLCYCLOPENTENE; 2 AMINO 1 CYANO 3 (4 METHYLBENZOYL) 4 (4 CHLOROPHENYL) 5,5 DIPHENYLCYCLOPENTENE; 2 AMINO 1 CYANO 3 (4 METHYLBENZOYL) 4 PHENYL 5,5 BIS(4 METHYLPHENYL)CYCLOPENTENE; 2 AMINO 1 CYANO 3 BENZOYL 4 PHENYL 5,5 BIS(4 METHYLPHENYL)CYCLOPENTENE; 2 AMINO 3 BENZOYL 1 CYANO 4 (3 BROMOPHENYL) 5,5 DIPHENYLCYCLOPENTENE; 2 AMINO 3 BENZOYL 1 CYANO 4 (4 CHLOROPHENYL) 5,5 DIPHENYLCYCLOPENTENE; 2 AMINO 3 BENZOYL 1 CYANO 4 (4 METHOXYPHENYL) 5,5 DIPHENYLCYCLOPENTENE; 2 AMINO 3 BENZOYL 1 CYANO 4 (4 METHYLPHENYL) 5,5 DIPHENYLCYCLOPENTENE; 2 AMINO 3 BENZOYL 1 CYANO 4,5,5 TRIPHENYLCYCLOPENTENE; 2 METHYL 2 N BUTYL 3,3 DIPHENYL 4 CYANO 5 AMINO 2,3 DIHYDROFURAN; 2 METHYL 2 N PENTYL 3,3 BIS(4 METHYLPHENYL) 4 CYANO 5 AMINO 2,3 DIHYDROFURAN; 2 METHYL 2 N PENTYL 3,3 DIPHENYL 4 CYANO 5 AMINO 5 AMINO 2,3 DIHYDROFURAN; 2 METHYL 2,3,3 TRIPHENYL 4 CYANO 5 AMINO 2,3 DIHYDROFURAN; 2,2 DIETHYL 3,3 DIPHENYL 4 CYANO 5 AMINO 2,3 DIHYDROFURAN; 2,2 PENTAMETHYLENE 3,3 BIS(4 METHYLPHENYL) 4 CYANO 5 AMINO 2,3 DIHYDROFURAN; 2,2 PENTAMETHYLENE 3,3 DIPHENYL 4 CYANO 5 AMINO 2,3 DIHYDROFURAN; 2,2 PENTAMETHYLENE 3,3 DIPHENYL 4 ETHOXYCARBONYL 5 AMINO 2,3 DIHYDROFURAN; AMINE; CHALCONE DERIVATIVE; CYCLOPENTENE DERIVATIVE; ETHYLENE DERIVATIVE; FURAN DERIVATIVE; KETONE; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; REDUCTION;

EID: 0043065595     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120021985     Document Type: Article

References (47)

1. (a) Girard, P.; Namy, J.L.; Kagan, H.B. J. Am. Chem. Soc. 1980, 102, 2693;
2. (b) Namy, J.L.; Girard, P.; Kagan, H.B. Nauv. J. Chim. 1977, 1, 5;
3. (c) Kagan, H.B. New. J. Chem. 1990, 14, 453.
4. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
5. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
6. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
7. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
8. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
9. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
10. 2, see: (a) Krief, A.; Laval, A.M. Chem Rev. 1999, 99, 745; (b) Molander, G.A. Acc. Chem. Res. 1998, 31, 603; (c) Molander, G.A.; Harris, C.R. Tetrahedron 1998, 54, 3321; (d) Molander, G.A.; Harris, C.R. Chem. Rev. 1996, 96, 307; (e) Imamota, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994; Chapter 4; (f) Molander, G.A. Chem. Rev. 1992, 92, 29; (g) Curran, D.P.; Fevig, T.L.; Jasperse, C.P.; Totleben, M.J. Synlett 1992, 943.
11. Kang, H.Y.; Hong, W.S. Tetrahedron Lett. 1995, 36, 7661.
12. (a) Yacovan, A.; Hoz, S. J. Org. Chem. 1997, 62, 771;
13. (b) Yacovan, A.; Hoz, S.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261.
14. (a) Rapoport, Z. Isr. J. Chem. 1970, 8, 749;
15. (b) Namy, J.L.; Souppe, J.; Kagan, H.B. Tetrahedron Lett. 1983, 24, 765.
16. (a) Zhou, L.H.; Zhang, Y.M. J. Chem. Soc. Perkin. Trans. 1 1998, 2399;
17. (b) Zhou, L.H.; Zhang, Y.M.; Shi, D.Q. Tetrahedron Lett. 1998, 39, 8491.
18. Xu, X.L.; Zhang, Y.M. J. Chem. Soc. Perkin. Trans. 1 2001, 2836.
19. (a) Dean, F.M.; Sargent, M.V. In Comprehensive Heterocyclic Chemistry, Bird, C.W., Cheeseman, G.W., Eds.; Pergamon Press: New York, 1984; Vol. 4, part 3, 531;
20. (b) Dean, F.M. In Advances in Heterocyclic Chemistry, Katritzky, A.R., Ed.; Academic Press: New York, 1982; Vol. 30, 167; Vol. 31, 237;
21. (b) Dean, F.M. In Advances in Heterocyclic Chemistry, Katritzky, A.R., Ed.; Academic Press: New York, 1982; Vol. 30, 167; Vol. 31, 237;
22. (c) Becker, K.B. Tetrahedron 1980, 36, 1717;
23. (d) Melibyan, G.G.; Sargsyan, A.B.; Mkrtchyan, D.A.; Azaryan, G.Kh.; Badanyan, Sh.O. Khim. Geterotsikl. Soedin. 1992, 4, 468.
24. (a) Marshall, J.A.; Sehon, C.A. J. Org. Chem. 1995, 60, 5966;
25. (b) Himeda, Y.; Hatanaka, M.; Ueda, I. J. Chem. Soc. Chem. Commun. 1995, 449;
26. (c) Baird, M.S.; Baxter, A.G.W.; Hoorfar, A.; Jefferies, I. J. Chem. Soc. Perkin Trans. 1 1991, 2575;
27. (d) Caesar, J.C.; Griffiths, D.V.; Griffiths, P.A.; Tebby, J.C. J. Chem. Soc. Perkin Trans. 1 1989, 2425;
28. (e) Wilson, I.F.; Tebby, J.C. J. Chem. Soc. Perkin Trans. 1 1972, 2830;
29. (f) Zbiral, E. Synthesis 1974, 775;
30. (g) Dean, F.M. Adv. Heterocycl. Chem. 1982, 30, 167;
31. (h) Schweizer, E.E.; Wehman, A.T.; Nycz, D.M. J. Org. Chem. 1973, 38, 1583;
32. (i) Schweizer, E.E.; Liehr, J.G. J. Org. Chem. 1968, 33, 583;
33. (j) Burgada, R.; Setton, R. The Chemistry of Organophosphorus Compounds, Patai, S., Hartley, F.R., Eds.; Wiley, 1994; Vol. 3, 231.
34. (a) Zhou, L.H.; Zhang, Y.M. Tetrahedron Lett. 1997, 38, 8063;
35. (b) Kagan, H.B.; Griard, P.; Namy, J.L. Tetrahedron 1981, 37(suppl 1), 175.
36. Cook, A.G. Enamines: Their Synthesis, Structure and Reaction; Marcel Dekker: New York, 1969.
37. (a) Stork, G.; Brizzolara, A.; Landesman, H.; Szmuszkovicz, J.; Terrell, R. J. Am. Chem. Soc. 1963, 85, 207;
38. (b) House, H.O. Modern Synthetic Reaction, 2nd Ed.; (W. Benjamin, California, 1972), 742 pp.
39. (a) Schaefer, J.P.; Bloomfield, J. J. Organic Reactions 1967, 15, 1;
40. (b) Seitz, G.; Monnighoff, H. Tetrahedron Lett. 1971, 12, 4889;
41. (c) Helmers, R.; Kaiser, W. Tetrahedron Lett. 1971, 12, 3853;
42. (d) Wawzonek, S.; Zigman, A.R.; Hansen, G.R. J. Electrochem. Soc. 1970, 117, 1351.
43. (a) Baron, H.; Remfry, F.G.P.; Thorpe, J.F. J. Chem. Soc. 1904, 85, 1726;
44. (b) Ziegler, K.; Eberle, E.; Ohlinger, M. Ann. 1933, 504, 94.
45. Yu, Y.P.; Lin, R.H.; Zhang, Y.M. Tetrahedron Lett. 1993, 34, 4547.
46. Campaigne, E.; Bulbenko, G.F.; Kreighbaum, W.E.; Mauloling, D.R. J. Org. Chem. 1962, 27, 4428.
47. Cragoe, E.J., Chargles, J.R.; Robb, M.; Sprague, J.M. J. Org. Chem. 1950, 15, 381.