Synthesis of new polyfunctional 2-pyrrolidinones from methyl 2-(carboethoxyhydroxymethyl)acrylate

Tetrahedron Letters

Volumn 48, Issue 31, 2007, Pages 5555-5559

  Morizur, Jean François ^a   Mathias, Lon J ^a  

^a Virginia Polytechnic Institute and State University   (United States)

Author keywords

2 Pyrrolidinone; Alkyl 2 (carboethoxyhydroxymethyl)acrylate; Baylis Hillman; Michael addition

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; AMINE; METHYL GROUP;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DIASTEREOISOMER; HYDROGEN BOND; INFRARED SPECTROSCOPY; MICHAEL ADDITION; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 34347343833     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.05.122     Document Type: Article

References (22)

1. Meyers A.I., and Snyder L. J. Org. Chem. 58 (1993) 36-42
2. Bergmann R., and Gericke R. J. Med. Chem. 33 (1990) 492-504
3. Corey E.J., and Li W.-D.Z. Chem. Pharm. Bull. 47 (1999) 1-10
4. Nilsson B.M., Ringdhal B., and Hacksell U.A. J. Med. Chem. 33 (1990) 580-584
5. Hanessian S., and Ratovelomanana V. Synlett (1990) 501-503
6. Russ P.L., and Caress E.A. J. Org. Chem. 41 (1976) 149-151
7. Kornet M.J., Thio P.A., and Tan S.I. J. Org. Chem. 33 (1968) 3637-3639
8. Ghelfi F., Bellesia F., Forti L., Ghirardini G., Grandi R., Libertini E., Montemaggi M.C., Pagnoni U.M., Pinetti A., De Buyck L., and Parsons A.F. Tetrahedron 55 (1999) 5839-5852
9. Cossy J., Cases M., and Pardo D.G. Synlett (1998) 507-509
10. Murakami S., Takemoto T., and Shimizu Z. J. Pharm. Soc. Jpn. 73 (1953) 1026-1028
11. Beltaïef I., Besbes R., Ben Amor F., Amri H., Villiéras M., and Villiéras J. Tetrahedron 55 (1999) 3949-3958
12. Arvanitis E., Motevalli M., and Wyatt P.B. Tetrahedron Lett. 37 (1996) 4277-4280
13. Felluga F., Pitacco G., Prodan M., Pricl S., Visintin M., and Valentin E. Tetrahedron: Asymmetry 12 (1999) 3241-3249
14. Fikentscher, R.; Hahn, E.; Kud, A.; Oftring, A. Ger. Patent DE 3444097 A1 19860605, 1986.
15. 2O: C, 50.59; H, 6.49. Found: C, 50.28; H, 6.28.
16. 4: C, 59.24; H, 8.70; N, 5.76. Found: C, 59.42; H, 8.71; N, 5.84.
17. Forster A., Fitremann J., and Renaud P. Tetrahedron Lett. 39 (1998) 7097-7100
18. Maiti G., and Roy S.C. J. Chem. Soc., Perkin Trans. 1 (1996) 403-404
19. Ghatak A., Sarkar S., and Ghosh S. Tetrahedron 53 (1997) 17335-17342
20. Mahato S.B., Siddiqui K.A.I., Bhattacharya G., Ghosal T., Miyahara K., Sholichin M., and Kawasaki T. J. Nat. Prod. 50 (1987) 245-247
21. 4: C, 57.62; H, 8.35; N, 6.11. Found: C, 57.35; H, 8.33; N, 6.03.
22. -1) 3351, 2960, 2935, 2870, 1741, 1729, 1685, 1654, 1277, 819.