Synthesis of 3-aminopyrrolidin-2-ones by an intramolecular reaction of aziridinecarboxamides

Tetrahedron

Volumn 52, Issue 29, 1996, Pages 9909-9924

  Funaki, Ikuo ^a   Thijs, Lambertus ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; AZIRIDINE DERIVATIVE; BICYCLO COMPOUND; BRIDGED PEPTIDE; ETHYLENE OXIDE; GAMMA LACTAM DERIVATIVE; LACTAM DERIVATIVE;

ARTICLE; CHEMICAL REACTION; NUCLEAR OVERHAUSER EFFECT; PEPTIDE SYNTHESIS; PRIORITY JOURNAL; PROTEIN CONFORMATION; STEREOCHEMISTRY; X RAY DIFFRACTION;

EID: 0030586126     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00523-6     Document Type: Article

References (63)

1. 1. For example, see: (a) Hruby, V. J. Trends Pharmacol. Sci. 1985, 6, 259.
2. (b) Veber, D. F.; Freidinger, R. M.; Perlow, D. S.; Paleveda, W. J., Jr.; Holly, F. W.; Strachan, R. G.; Nutt, R. F.; Arison, B. H.; Homnick, C; Randall, W. C.; Glitzer, M. S.; Saperstein, R.; Hirschmann, R. Nature 1981, 292, 55.
3. (c) Freidinger, R. M.; Perlow, D. S.; Veber, D. F.; Brooks, J. R.; Saperstein, R. Science 1980, 210, 656.
4. (d) Ward, P.; Ewan, G. B.; Jordan, C. C.; Ireland, S. J.; Hagan, R. M.; Brown, J. R. J. Med. Chem. 1990, 33, 1848.
5. (e) Hinds, M. G.; Richards, N. G. J.; Robinson, J. A. J. Chem. Soc., Chem. Commun. 1988, 1447.
6. (f) Aebi, J. D.; Guillaume, D.; Dunlap, B. E.; Rich, D. H. J. Med. Chem. 1988, 31, 1805.
7. (g) Olson, G. L.; Voss, M. E.; Hill, D. E.; Kahn, M.; Madison, V. S.; Cook, C. M. J. Am. Chem. Soc. 1990, 112, 323.
8. (h) Smith, A. B., III; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. Ibid. 1992, 114, 10672.
9. (i) Callahan, J. F.; Newlander, K. A.; Burgess, J. L.; Eggleston, D. S.; Nichols, A.; Wong, A.; Huffman, W. F. Tetrahedron 1993, 49, 3479.
10. (j) Genin, M. J.; Gleason, W. B.; Johnson R. L. J. Org. Chem. 1993, 58, 860.
11. (k) Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J. Tetrahedron Lett. 1993, 34, 1665.
12. (l) Ripka, W. C.; De Lucca, G. V.; Bach, A. C., II; Pottorf, R. S.; Blaney, J. M. Tetrahedron 1993, 49, 3593.
13. (m) Genin, M. J.; Ojala, W. H.; Gleason, W. B.; Johnson, R. L.; J. Org. Chem. 1993, 58, 2334.
14. (n) Sreenivasan, U.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 256.
15. (o) Williams, B. J.; Curtis, N. R.; McKnight, A. T.; Maguire, J. J.; Young, S. C.; Veber, D. F.; Baker, R. Ibid, 1993, 36, 2.
16. (p) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Weller, H. N.; Pan, Y. Y.; Malley, M.; DiMarco, J. D. J. Am. Chem. Soc. 1994, 116, 2348.
17. (q) Gante, J. Angew. Chemie 1994, 106, 1780.
18. 2. (a) Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 47, 104.
19. (b) Garvey, D. S.; May, P. D.; Nadzan, A. M. Ibid, 1990, 55, 936.
20. 3. For synthesis of 3-amino-3-substituted-pyrrolidin-2-ones, see: (a) Freidinger, R. M. J. Org. Chem. 1985, 50, 3631.
21. (b) Holladay, M. W.; Nadzan, A. M. Ibid, 1991, 56, 3900.
22. (c) Zydowsky, T. M.; Dellaria, Jr., J. F.; Nellans, H. N. Ibid, 1988, 53, 5607.
23. (d) Thaisrivongs, S.; Pals, D. T.; Turner, S. R.; Kroll, L. T. J. Med. Chem. 1988, 31, 1369.
24. (e) Abell, A. D.; Taylor, J. M. J. Org. Chem. 1993, 58, 14.
25. 4. (a) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881. Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1.
26. 4. (a) Legters, J.; Thijs, L.; Zwanenburg, B. Tetrahedron Lett. 1989, 30, 4881. Legters, J.; Thijs, L.; Zwanenburg, B. Recl. Trav. Chim. Pays-Bas 1992, 111, 1.
27. (b) Legters, J. Ph.D. Thesis; 1991. University of Nijmegen.
28. 5. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
29. 6. Bergmeier, S. C.; Lee, W. K.; Rapoport, H. J. Org. Chem., 1993, 58, 5019.
30. 7. Fitremann, J.; Duréault, A.; Depezay, J-C. Tetrahedron Lett., 1994, 35, 1201.
31. 8. Aza-[2,3]-Wittig rearrangement of vinylaziridines, see: Åhman, J.; Somfai, P. J. Am. Chem. Soc., 1994, 116, 9781; Åhman, J.; Somfai, P. Tetrahedron Lett. 1995, 36, 303; Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. Ibid, 1995, 36, 3557.
32. 8. Aza-[2,3]-Wittig rearrangement of vinylaziridines, see: Åhman, J.; Somfai, P. J. Am. Chem. Soc., 1994, 116, 9781; Åhman, J.; Somfai, P. Tetrahedron Lett. 1995, 36, 303; Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. Ibid, 1995, 36, 3557.
33. 8. Aza-[2,3]-Wittig rearrangement of vinylaziridines, see: Åhman, J.; Somfai, P. J. Am. Chem. Soc., 1994, 116, 9781; Åhman, J.; Somfai, P. Tetrahedron Lett. 1995, 36, 303; Coldham, I.; Collis, A. J.; Mould, R. J.; Rathmell, R. E. Ibid, 1995, 36, 3557.
34. 9. (a) Deyrup, J. A. in Heterocyclic Compounds, vol. 42, part 1, "Small Ring Heterocycles", pp. 115-119, Hassner, A. ed., Wiley Interscience, New York, 1983.
35. (b) Bouayad, Z.; Chanet-Ray, J.; Ducher, S.; Vessiére, R. J. Heterocyclic Chem. 1991, 28, 1757.
36. (c) Stamm, H.; Schneider, L. Chem. Ber. 1975, 108, 500.
37. (d) Hassner, A.; Kascheres, A. Tetrahedron Lett. 1970, 4623.
38. (e) Baldwin, J. E.; Adlington, R. M.; O'Neil, I. A.; Schofield, C.; Spivey, A. C.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1989, 1852.
39. 10. (a) Nakajima, K.; Neya, M.; Yamada, S.; Okawa, K. Bull. Chem. Soc. Jpn. 1982, 55, 3049.
40. (b) Baldwin, J. B.; Adlington, R. M.; Robinson, N. G. J. Chem. Soc., Chem. Commun. 1987, 153.
41. (c) Sato, K.; Kozikowsky, A. P. Tetrahedron Lett. 1989, 30, 4073.
42. (d) Shima, I.; Shimazaki, N.; Imai, K.; Hemmi, K.; Hashimoto, M. Chem. Pharm. Bull. 1990, 38, 564.
43. (e) Okawa, K.; Nakajima, K.; Tanaka, T.; Neya, M. Bull. Chem. Soc.Jpn. 1982, 55, 174.
44. (f) Nakajima, K.; Tanaka, T.; Morita, K.; Okawa, K. Ibid, 1980, 55, 283.
45. (g) Parry, R. J.; Naidu, M. V. Tetrahedron Lett. 1983, 24, 1133.
46. (h) Vaultier, M.; Ouali, M. S.; Carrié, R. Bull. Soc. Chim. Fr. Part II, 1979, 343.
47. 11. The X-ray data will be submitted for publication separately: Smits, J.; Beurskens, P. T.; Israel, O. R.; Funaki, I.; Thijs, L.; Zwanenburg, B. Acta Crystallographica Sec. C.
48. 12. Ho, T-L. Chem. Rev. 1975, 75, 1.
49. 13. (a) Intramolecular attack at the C-2 position in aziridinecarboxamides will be published in due time. For intramolecular ring-opening reactions of epoxycarboxamides, see:
50. (b) Shiozaki, M.; Ishida, N.; Hiraoka, T.; Yanagisawa, H. Tetrahedron Lett. 1981, 22, 5205.
51. (c) Yanagisawa, H.; Ando, A.; Shiozaki, M.; Hiraoka, T. Ibid, 1983, 24, 1037.
52. (d) Chackalamannil, S.; Fett, N.; Kirkup, M.; Afonso, A.; Ganguly, A. K. J. Org. Chem. 1988, 53, 450.
53. (e) Hanessian, S; Bedeschi, A.; Battistini, C.; Mongelli, N. J. Am. Chem. Soc. 1985, 107, 1438.
54. (f) Häbich, D.; Hartwig, W. Tetrahedron Lett. 1987, 28, 781.
55. 14. For full details, see: Funaki, I. Thesis University of Nijmegen, 1996. 2D-NOESY NMR study application to 1,3-imidazolidin-5-ones, see: Grozinger, K. G.; Kriwacki, R. W.; Leonard, S. F.; Pitner, T. P. J. Org. Chem. 1993, 55, 709.
56. 14. For full details, see: Funaki, I. Thesis University of Nijmegen, 1996. 2D-NOESY NMR study application to 1,3-imidazolidin-5-ones, see: Grozinger, K. G.; Kriwacki, R. W.; Leonard, S. F.; Pitner, T. P. J. Org. Chem. 1993, 55, 709.
57. 15. Cruickshank, P. A.; Fishman, M. J. Org. Chem. 1969, 34, 4060.
58. 16. Electronic effects of substituents on intramolecular epoxide ring-opening reactions, see: Nicolaou, K. C.; Prasad, C. V. C.; Somers, P. K.; Hwang, C.-K. J. Am. Chem. Soc. 1989, 111, 5330.
59. 17. Krapcho, A. P.; Lovey, A. J. Tetrahedron Lett. 1973, 957.
60. 18. Kanemasa, S.; Tatsukawa, A.; Wada, E. J. Org. Chem. 1991, 56, 2875.
61. 19. Von Arx, E.; Faupel, M.; Brugger, M. J. J. Chromatogr. 1976, 120, 224.
62. 20. Org. Synth., Collective Vol., V, pp. 373-378.
63. 21. Luo, F.-T.; Negishi, E.-I. J. Org. Chem. 1985, 50, 4762.