Synthetic approaches to 2-pyrrolidinone-5-carboxaldehyde

Synthetic Communications

Volumn 26, Issue 16, 1996, Pages 3137-3150

  Deskus, Jeffrey ^a   Smith, Michael B ^a   Simandan, Tiberiu ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDINONE 5 CARBOXALDEHYDE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030057832     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608004620     Document Type: Article

References (30)

1. (a) Keusenkothen, P.F.; Smith, M.B. J. Chem. Soc., Perkin Trans, 1, 1984, 2485;
2. (b) Keusenkothen, P.F.; Smith, M.B. Idem Tetrahedron, 1992, 48, 2977;
3. (c) Keusenkothen, P.F.; Smith, M.B. Idem Tetrahedron Lett., 1989, 30, 3369.
4. Kwon, T.W.; Keusenkothen, P.; Smith, M.B. J. Org. Chem., 1992, 57, 6169.
5. (a) Zezza, C.A.;Smith, M.B. J. Org. Chem., 1988, 53, 1161;
6. (b) Zezza, C.A.;Smith, M.B. Idem Synth. Commun., 1987, 17, 729.
7. Menezes, R.F., Zezza, C.A.; Sheu, J.L.; Smith, M.B. Tetrahedron Lett., 1989, 30, 3295.
8. Smith, M.B.; Dembofsky, B.T.; Son, Y.C. J. Org. Chem., 1994, 59, 1719.
9. Kwon, T.W.; Smith, M.B. Synth. Commun., 1992, 22, 2865.
10. Silverman, R.B.; Levy, M.A. J. Org. Chem., 1980, 45, 815.
11. Smith, M.B.; Zezza, C.A. Org. Mass Spectrom., 1988, 23, 285.
12. Ratcliffe, R.; Rodehorst, R. J. Org. Chem., 1970, 35, 4000.
13. Corey, E.J.; Suggs, J.W. Tetrahedron Lett., 1975, 2647.
14. Corey, E.J.; Schmidt, G. Tetrahedron Lett., 1975, 399.
15. Pfitzner, K.E.; Moffatt, J.G. J. Am. Chem. Soc., 1965, 87, 5661.
16. Moffatt, J.G. in Oxidation; Vol. 2, pp. 1-64, Augustine, R.L.; D.J. Trecker, D.J. (Eds.); Marcel Dekker, New York, 1971.
17. (a) Mancuso, A.J.; Swern, D. Synthesis, 1981, 165;
18. (b) Mancuso, A.J.; Huang, S.L.; Swern, D. J. Org. Chem., 1978, 43, 2480.
19. (a) Onodera, K.; Hirano, S.; Kashimura, N. J. Am. Chem. Soc., 1965, 87, 4651;
20. (b) Taber, D.F.; Amedio, J.C.; Jung, K.Y. J. Org. Chem., 1987, 52, 5621.
21. Albright, J.D.; Goldman, L. J. Am. Chem. Soc., 1967, 89, 2416.
22. a) Corey, E.J.; Kim, C.U. J. Am. Chem. Soc., 1972, 94, 7586;
23. (b) Corey, E.J.; Kim, C.U. Idem, J. Org. Chem., 1973, 38, 1233.
24. This reagent was kindly provided by Professor J.M. Bobbitt. See: Ma, Z.; Bobbitt, J.M. J. Org. Chem., 1991, 56, 6110.
25. (a) Cainelli, G.; Cardillo, G.; Orena, M.; Sandri, S. J. Am. Chem. Soc., 1976, 98, 6737;
26. (b) Wade, L.G.; Stell, L.M. J. Chem. Educ., 1980, 57, 438.
27. Yoon, N.M.; Gyoung, Y.S. J. Org. Chem., 1985, 50, 2443.
28. Weissman, P.M.; Brown, H.C. J. Org. Chem., 1966, 31, 283.
29. (a) Cha, J.S.; Min, S.J.; Lee, J.C.; Lee, H.S.; Lee, S.E. Org. Prep. Proceed. Int., 1992, 24, 335;
30. (b) Cha, J.S.; Kwon, S.S. J. Org. Chem., 1987, 52, 5486.