A simple and efficient chlorination reaction of heterocyclic ketene aminals

Synthetic Communications

Volumn 29, Issue 23, 1999, Pages 4241-4249

  Liu, Bo ^a   Wang, Mei Xiang ^a   Huang, Zhi Tang ^a  

^a INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; KETENE DERIVATIVE; TOSYLCHLORAMIDE SODIUM;

ARTICLE; CHLORINATION; DATA ANALYSIS; ELECTRON TRANSPORT; HALOGENATION; MICROANALYSIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0032716138     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919908085897     Document Type: Article

References (21)

1. For a review see, Huang, Z.-T. and Wang, M.-X. Heterocycles, 1994, 37, 1233.
2. Wang, M.-X., Liang, J.-M. and Huang, Z.-T. J. Chem. Res.(S), 1994, 166; J. Chem. Res.(M), 1994, 1001.
3. Wang, M.-X., Liang, J.-M. and Huang, Z.-T. J. Chem. Res.(S), 1994, 166; J. Chem. Res.(M), 1994, 1001.
4. Jones, R. C. F., Patel, P., Hirst, S. C. and Smallridge, M. J. Tetrahedron, 1998, 54, 6191; Jones, R. C. F. and Smallridge, M. J. Tetrahedron Lett., 1988, 29, 5005; Huang, Z.-T. and Liu, Z.-R. Heterocycles, 1986, 24, 2247; Huang, Z.-T. and Tzai, L.-H. Chem. Ber., 1986, 119, 2208; Gupta, A. K., Ila, H. and Junjapa, H. Synthesis, 1988, 285; Huang, Z.-T. and Wang, X.-J. Tetrahedron Lett., 1987, 28, 1527.
5. Jones, R. C. F., Patel, P., Hirst, S. C. and Smallridge, M. J. Tetrahedron, 1998, 54, 6191; Jones, R. C. F. and Smallridge, M. J. Tetrahedron Lett., 1988, 29, 5005; Huang, Z.-T. and Liu, Z.-R. Heterocycles, 1986, 24, 2247; Huang, Z.-T. and Tzai, L.-H. Chem. Ber., 1986, 119, 2208; Gupta, A. K., Ila, H. and Junjapa, H. Synthesis, 1988, 285; Huang, Z.-T. and Wang, X.-J. Tetrahedron Lett., 1987, 28, 1527.
6. Jones, R. C. F., Patel, P., Hirst, S. C. and Smallridge, M. J. Tetrahedron, 1998, 54, 6191; Jones, R. C. F. and Smallridge, M. J. Tetrahedron Lett., 1988, 29, 5005; Huang, Z.-T. and Liu, Z.-R. Heterocycles, 1986, 24, 2247; Huang, Z.-T. and Tzai, L.-H. Chem. Ber., 1986, 119, 2208; Gupta, A. K., Ila, H. and Junjapa, H. Synthesis, 1988, 285; Huang, Z.-T. and Wang, X.-J. Tetrahedron Lett., 1987, 28, 1527.
7. Jones, R. C. F., Patel, P., Hirst, S. C. and Smallridge, M. J. Tetrahedron, 1998, 54, 6191; Jones, R. C. F. and Smallridge, M. J. Tetrahedron Lett., 1988, 29, 5005; Huang, Z.-T. and Liu, Z.-R. Heterocycles, 1986, 24, 2247; Huang, Z.-T. and Tzai, L.-H. Chem. Ber., 1986, 119, 2208; Gupta, A. K., Ila, H. and Junjapa, H. Synthesis, 1988, 285; Huang, Z.-T. and Wang, X.-J. Tetrahedron Lett., 1987, 28, 1527.
8. Jones, R. C. F., Patel, P., Hirst, S. C. and Smallridge, M. J. Tetrahedron, 1998, 54, 6191; Jones, R. C. F. and Smallridge, M. J. Tetrahedron Lett., 1988, 29, 5005; Huang, Z.-T. and Liu, Z.-R. Heterocycles, 1986, 24, 2247; Huang, Z.-T. and Tzai, L.-H. Chem. Ber., 1986, 119, 2208; Gupta, A. K., Ila, H. and Junjapa, H. Synthesis, 1988, 285; Huang, Z.-T. and Wang, X.-J. Tetrahedron Lett., 1987, 28, 1527.
9. Jones, R. C. F., Patel, P., Hirst, S. C. and Smallridge, M. J. Tetrahedron, 1998, 54, 6191; Jones, R. C. F. and Smallridge, M. J. Tetrahedron Lett., 1988, 29, 5005; Huang, Z.-T. and Liu, Z.-R. Heterocycles, 1986, 24, 2247; Huang, Z.-T. and Tzai, L.-H. Chem. Ber., 1986, 119, 2208; Gupta, A. K., Ila, H. and Junjapa, H. Synthesis, 1988, 285; Huang, Z.-T. and Wang, X.-J. Tetrahedron Lett., 1987, 28, 1527.
10. Jones, R. C. F., Patel, P., Hirst, S. C. and Turner, I. Tetrahedron, 1997, 53, 11781; Wang, M.-X. and Huang, Z.-T. J. Org. Chem., 1995, 60, 2807; Huang, Z.-T. and Wang, M.-X. J. Chem. Soc., Perkin Trans. 1, 1993, 1085; Huang, Z.-T. and Liu, Z.-R. Chem. Ber., 1989, 122, 95.
11. Jones, R. C. F., Patel, P., Hirst, S. C. and Turner, I. Tetrahedron, 1997, 53, 11781; Wang, M.-X. and Huang, Z.-T. J. Org. Chem., 1995, 60, 2807; Huang, Z.-T. and Wang, M.-X. J. Chem. Soc., Perkin Trans. 1, 1993, 1085; Huang, Z.-T. and Liu, Z.-R. Chem. Ber., 1989, 122, 95.
12. Jones, R. C. F., Patel, P., Hirst, S. C. and Turner, I. Tetrahedron, 1997, 53, 11781; Wang, M.-X. and Huang, Z.-T. J. Org. Chem., 1995, 60, 2807; Huang, Z.-T. and Wang, M.-X. J. Chem. Soc., Perkin Trans. 1, 1993, 1085; Huang, Z.-T. and Liu, Z.-R. Chem. Ber., 1989, 122, 95.
13. Jones, R. C. F., Patel, P., Hirst, S. C. and Turner, I. Tetrahedron, 1997, 53, 11781; Wang, M.-X. and Huang, Z.-T. J. Org. Chem., 1995, 60, 2807; Huang, Z.-T. and Wang, M.-X. J. Chem. Soc., Perkin Trans. 1, 1993, 1085; Huang, Z.-T. and Liu, Z.-R. Chem. Ber., 1989, 122, 95.
14. Huang, Z.-T. and Wang, M.-X. J. Org. Chem., 1992, 57, 184.
15. Huang, Z.-T. and Wang, M.-X. Synth. Commun., 1991, 21, 1167; 1909.
16. Results of the reactions of heterocyclic ketene aminals with nitrilimines and nitrile ylides will be published elsewhere.
17. For a recent review see, Rappoport, Z. (ed.) "The Chemistry of Enamines", John Wiley & Sons, Chichester, UK, 1994, pp. 788-794.
18. Tieman, C. H., Kollmeyer, W. D. and Roman, S. A. US Pat. 3,971,774 (1976). Chem. Abstr., 1977, 86, 5460k.
19. Huang, Z.-T. and Wamhoff, H. Chem. Ber., 1984, 117, 1856.
20. El-Saghier, A. M. M., Maihub, A. A. and Al-Shirayda, H. A. Synth. Commun., 1997, 27, 2433.
21. The chlorine atom might be displaced by nucleophiles, see an example in reference 11.