(Chloromethylene)dimethylammonium chloride: A highly efficient reagent for the synthesis of β-lactams from β-amino acids

Journal of Chemical Research

Volumn , Issue 11, 2005, Pages 705-707

  Kanwar, Seema ^a   Sharma, Sain D ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

(chloromethylene)dimethylammonium chloride; Cyclodehydration; Intramolecular cyclisation; amino acids; lactams

Indexed keywords

EID: 28944435241     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823405774909414     Document Type: Article

References (20)

1. W. Durckheimer, J. Blumbach, R. Lattrell and K.H. Scheunemann, Angew. Chem. Int. Ed. Engl., 1985, 24, 180.
2. T.V. Stezhko, S. Y. Skachilova, and M.G. Pleshkov, Zh. Org. Khim., 1974, 10, 1556.
3. G.I. George, The Organic Chemistry of b-lactams, VCH, New York 1993. pp. 295.
4. S.D. Sharma and P.K. Gupta, Tetrahedron Lett., 1978, 4587.
5. S.D. Sharma and S. Bhaduri, J. Chem. Res. (S), 2001, 321.
6. S.D. Sharma, R.D. Anand and G. Kaur, Synth. Commun., 2004, 34, 1.
7. E. Campaigne and W.L. Archer, J. Am. Chem. Soc., 1953, 75, 989.
8. W. Treihs, H.J. Neupert and J. Hiebsch, Chem. Ber., 1959, 92, 141.
9. P.A. Procopiou, A.C. Brodie, M.J. Deal and D.F. Hayman, Tetrahedron Lett., 1993, 34, 7483.
10. P.A. Procopiou, A.C. Brodie, M.J. Deal and D.F. Hayman, J. Chem. Soc. Perkin Trans. 1, 1996, 2249.
11. M. Zaoral and Z. Arnold, Tetrahedron Lett., 1960, 9.
12. H. Eilingsfeld, M. Seefelder and H. Weidinger, Angew Chem., 1960, 72, 836.
13. D.R. Hepburn and H.R. Hudson, J. Chem. Soc., Perkin Trans. 1, 1976, 754.
14. A.G.M. Barrett, N. Koike and A. Procopiou, J. Chem. Soc. Chem. Commun., 1995, 1403.
15. A.G. M. Barrett, D.C. Braddock, R.A. James and A. Procopiou, J. Chem. Soc. Chem. Commun., 1997, 433.
16. F.F. Blicke and W.A. Gould, J. Org. Chem., 1958, 23, 1102.
17. A. Zilkha and J. Rivlin, J. Org. Chem., 1958, 23, 94.
18. T.B. Johnson and J.E. Lovak, J. Am. Chem. Soc., 1936, 58, 299.
19. R.W. Holley and A.D.Holley, J. Am. Chem. Soc., 1949, 71, 2129.
20. R.W. Holley and A.D. Holley, J. Am. Chem. Soc., 1949, 71, 2124.