Cyclisation at very high temperature. Thermal transformations of N-alkyl and N,N-dialkyl cinnamic amides into pyrrolidin-2-ones under FVT conditions

Tetrahedron Letters

Volumn 46, Issue 17, 2005, Pages 3093-3095

  Leśniak, Stanisław ^a   Pasternak, Beata ^a  

^a UNIVERSITY OF LODZ   (Poland)

Author keywords

Amides; Cyclisation; Flash vacuum thermolysis; lactams

Indexed keywords

AMIDE; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; HIGH TEMPERATURE; ISOMERIZATION; REACTION ANALYSIS; THERMAL ANALYSIS; VACUUM;

EID: 15944371943     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.004     Document Type: Article

References (20)

1. J.-L. Ripoll, and Y. Vallee Synthesis 1993 659 677
2. H. Bibas, R. Koch, and C. Wentrup J. Org. Chem. 63 1998 2619 2626
3. 3. The solvent was removed under reduced pressure and the products were purified chromatographically on silica gel and by recrystallisation
4. T. Sato, N. Chono, H. Ishibashi, and M. Ikeda J. Chem. Soc., Perkin Trans. 1 1995 1115 1120
5. 2 (191.23): C, 69.09; H, 6.85; N, 7.32. Found: C, 69.22; H, 6.84; N, 7.11
6. 17NO (203.29): C, 76.81; H, 8.43; N, 6.89. Found: C, 76.84; H, 8.31; N, 6.72
7. M. Langlois Bull. Soc. Chim. Fr. 1971 2976 2980
8. 17NO (251.33): C, 81.24; H, 6.82; N, 5.57. Found: C, 81.01; H, 7.06; N, 5.29
9. N.K. Kee Tetrahedron Lett. 38 1997 5091 5094
10. V.M. Potapov, R.A. Gracheva, S.A. Savina, and L.A. Sivova J. Org. Chem. USSR (Engl. Transl.) 25 1989 1694 1699
11. Zh. Org. Khim. RU 1989 1876 1881
12. M. Black, J.I.G. Cadogan, and H. McNab J. Chem. Soc., Perkin Trans. 1 1994 155 159
13. M.S. Manhas, M. Ghosh, and A.K. Bose J. Org. Chem. 55 1990 575 580
14. A.K. Bose, M.S. Manhas, M. Ghosh, M. Shah, V.S. Raju, S.S. Bari, S.N. Newaz, B.K. Banik, A.G. Chaudhary, and K.J. Barakat J. Org. Chem. 56 1991 6968 6970
15. F.H. Van der Steen, and G. Van Koten Tetrahedron 47 1991 7503 7524
16. This efficient one-pot procedure is based on the treatment of the imine with corresponding acid chloride in toluene at room temperature, in the presence of triethylamine. T.R. Govindachari, P. Chinnasamy, S. Rajewari, S. Chandrasekaran, M.S. Premila, K. Nagarajan, and B.R. Pai Heterocycles 22 1984 585 655
17. J.S. Sandhu, and B. Sain Heterocycles 26 1987 777 818
18. B. Alcaide, Y. Martin-Cantalejo, J. Plumet, J. Rodriguez-Lopez, and M.A. Sierra Tetrahedron Lett. 32 1991 803 806
19. Ch. Kashima, K. Fukusaka, and K. Takahashi J. Heterocycl. Chem. 34 1997 1559 1565
20. C.R. Rasmussen, J.F. Gardocki, J.N. Plampin, B.E. Twardzik, A.J. Reynolds, A.J. Molinari, N. Schwartz, W.W. Bennetts, B.E. Price, and J. Marakowski J. Med. Chem. 21 1978 1044 1047