N,N-(dimethylamino)-2-pyrrolidinones from the rearrangement of N-allyl-N',N'-dimethyl-2,2-dichlorohydrazides promoted by CuCl-N,N,N',N'-tetramethylethylendiamine

Journal of Organic Chemistry

Volumn 65, Issue 19, 2000, Pages 6249-6253

  Ghelfi, Franco ^a   Parsons, Andrew F ^b  

^a UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^b UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; HYDRAZIDE DERIVATIVE;

CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; NOTE; STRUCTURE ANALYSIS;

EID: 0034703439     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0004153     Document Type: Note

References (53)

1. Galeazzi, R.; Mobbili, G.; Orena, M. Targets Heterocycles 1997, 1, 355.
2. (a) Gouliaev, A. H.; Senning, A. Brain Res. Rev. 1994, 19, 180.
3. (b) Hulme, C.; Moriarty, K.; Huang, F-C.; Mason, J.; McGarry, D.; Labaudiniere, R.; Souness, J.; Djiuric. S. Bioorg. Med. Chem. Lett. 1998, 8, 399.
4. (c) Silverman, R. B., II. Farmaco 1997, 52, 343.
5. Okayama, T.; Araki, S.; Miyamae, T.; Morita, Y.; Morikawa, T.; Hagiwara, M. Arzneim.-Forsch. / Drug. Res. 1997, 47 (II), 1023.
6. Herdei, C.; Hubmann, H. P. Tetrahedron Asymmetry 1992, 3, 1213.
7. Giambastiani, G.; Pacini, B.; Porcelloni, M.; Poli. G. J. Org. Chem. 1998, 63, 804.
8. Curran, D. P.; Porter, N.A.; Giese, B. Stereochemistry of Radical Reactions; VCH: Weinheim, 1996.
9. Quirante, J.; Escolano, C.;, Costejà, L.; Bonjoch, J. Tetrahedron Lett. 1997, 38, 6901.
10. Lipp, D.; Kozakiewicz, J. Encyclopedia of Chemical Technology, 4th ed.; Wiley: New York, 1991; p 266.
11. (a) Ishibashi, H.; Sato, T.; Ikeda, M. J. Synth. Org. Chem. Jpn. 1995, 53, 85.
12. (b) Nagashima, H.; Itoh, K. J. Synth. Org. Chem. Jpn. 1995, 53, 298.
13. (a) Parsons, A.F.; Taylor, R. J. K. J. Chem. Soc., Perkin Trans. 1 1994, 1945.
14. (b) Sato, T.; Tsujimoto, K.; Matsubayashi, K.; Ishibashi, H.; Ikeda, M. Chem. Pharm. Bull. 1992, 40, 2308.
15. (a) Nagashima, H.; Ozaki, N.; Ishii, M.; Seki, K.; Washiyama, M.; Itoh, K. J. Org. Chem. 1993, 58, 464.
16. (b) Rachita, M.A.; Slough, G.A. Tetrahedron Lett. 1993, 34, 6821-6824.
17. (c) Ikeda, M.; Teranishi, H.; Nozaki, K.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1 1998, 1691.
18. (d) Jasperse, C. P.; Curran, D.P.; Fevig, T. L. Chem. Rev. 1991, 91, 1237.
19. (e) Benedetti, M.; Forti, L.; Ghelfi, F.; Pagnoni, U. M.; Ronzoni, R. Tetrahedron 1997, 41, 14031.
20. (f) Ghelfi, F.; Bellesia, F.; Forti, L.; Ghirardini, G.; Grandi, R.; Libertini, E.; Montemaggi, M.C.; Pagnoni, U. M.; Pinetti, A.; De Buyck, L.; Parsons, A. F. Tetrahedron 1999, 55, 5839.
21. Clark, A. J.; Filik, R.P.; Thomas, G. H. Tetrahedron Lett. 1999, 40, 4885.
22. Curran, D.P.; Tamine, J. J. Org. Chem. 1991, 56, 2746.
23. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
24. (a) Bryans, J. S.; Large, J. M.; Parsons, A.F. Tetrahedron Lett. 1999, 4, 3487.
25. (b) Bryans, J.S.; Large, J. M.; Parsons, A. F. J. Chem. Soc., Perkin Trans. 1 1999, 2897.
26. Iwamatsu, S.; Matsubara, K.; Nagashima, H. J. Org. Chem. 1999, 64, 9625.
27. Forti, L.; Ghelfi, F.; Munari, F.; Pagnoni, U. M. Tetrahedron 1995, 45, 12285.
28. Gigg, R.; Conant, R. Carbohydr. Res. 1982, 100, C5.
29. (a) Naito, T.; Honda, Y.; Bhavakul, V.; Yamaguchi, S.; Fujiwara, A.; Miyata, O.; Ninomiya, I. Chem. Pharm. Bull. 1997, 45, 1932.
30. (b) Webster, F. X.; Millar, J. G.; Silverstein, R. M. Tetrahedron Lett. 1986, 27, 4941.
31. (c) Sugasawa, S.; Fujii, T. Chem. Pharm. Bull. 1958, 6, 587.
32. Repič, O. Principles of Process Research and Chemical Development in the Pharmaceutical Industry; Wiley: New York, 1998; p 8.
33. (a) Golden, D. M.; Solly, R. K.; Gac, N. A.; Benson, S. W. J. Am. Chem. Soc. 1972, 94, 363.
34. (b) Benson, S. W.; O'Neal, H. E. Kinetic Data on Gas-Phase Unimolecular Reactions; NSRDS-NBS, 1970; p 21.
35. (c) See also: Marshalkin, M. F.; Yakhontov, L. N. Russ. Chem. Rev. 1986, 55, 1016.
36. Perri, S. T.; Slater, S. C.; Toske, S. G.; White, J. D. J. Org. Chem. 1990, 55, 6037.
37. Butler, D. E.; Meyer, R. F.; Alexander, S. M.; Bass, P.; Kennedy, J. A. J. Med. Chem. 1973, 16, 49.
38. Kornet, M. J. J. Pharm. Sci. 1984, 73, 405.
39. Duffy, K. J.; Ridgers, L. H.; Desjarlais, R. L.; Tomaszek, T. A.; Bossard, M. J.; Thompson, S. K.; Keenan, R. M.; Veber, D. F. Bioorg. Med. Chem. Lett. 1999, 9, 1907.
40. Yaegashi, T.; Sawada, S.; Furuta, T.; Yokokura, T.; Yamaguchi, K.; Miyasaka, T. Chem. Pharm. Bull. 1993, 41, 971.
41. Matsumoto, Y.; Tsuzuki, R.; Matsuhisa, A.; Takayama, K.; Yoden, T.; Uchida, W.; Asano, M.; Fujita, S.; Yanagisawa, I.; Fujikura, T. Chem. Pharm. Bull. 1996, 44, 103.
42. (a) Sarkar, T. K.; Gangopadhyay, P.; Satapathi, T. K. Tetrahedron Lett. 1999, 40, 395.
43. (b) Vedejs, E.; Meier, G. P. Tetrahedron Lett. 1979, 20, 4185.
44. Konig, K. H.; Zeeh, B. Chem. Berichte 1970, 103, 2052.
45. Iwamatsu, S.; Kondo, H.; Matsubara, K.; Nagashima, H. Tetrahedron 1999, 55, 1687.
46. The cis isomer carries the prior groups on the same face; instead the contrary is true for the trans one. See: Rachita, M. A.; Slough, G. A. Tetrahedron Lett. 1993, 34, 6821.
47. Denmark, S. E.; Nicaise, O.; Edwards, J. P. J. Org. Chem. 1990, 55, 6219.
48. (a) Hinman, R. L. J. Org. Chem. 1957, 22, 148.
49. Burk, M.J.; Feaster,. J. E. J. Am. Chem. Soc. 1992, 114, 6266.
50. Ethyl acetate can also successfully replace acetonitrile in the rearrangement of N-allyl-N-benzyl-2,2-dichloroamides.
51. Bellesia, F.; Boni, M.; Ghelfi, F.; Pagnoni, U. M. Tetrahedron Lett. 1994, 35, 2961.
52. Bellesia, F.; De Buyck, L.; Ghelfi, F. Synlett 2000, 146.
53. It is imperative that the hydrazide is completely deprotonated otherwise the cyclization yields are considerably reduced.