Elimination of sulfur dioxide in alkanesulfonamides. Formation of 2-arylhydrazono-3,3,3-trifluoropropylamines from 2-arylhydrazono-3,3,3-trifluoropropanesulfonamides

Synthesis

Volumn , Issue 8, 1997, Pages 866-868

  Takahashi, Masahiko ^a   Muta, Shigeru ^a  

^a IBARAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARYLHYDRAZONO 3,3,3 TRIFLUOROPROPYLAMINE DERIVATIVE; SULFONAMIDE; SULFUR DIOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030819167     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1287     Document Type: Article

References (19)

1. Reviews on fluorine-containing heterocycles: Burger, K.; Wucherpfenning, U.; Brunner, E. In Advances in Heterocyclic Chemistry Vol. 60; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Silvester, M. J. In Advances in Heterocyclic Chemistry Vol. 59; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Elguero, J.; Fruchier, A.; Jagerovic, N.; Werner, A. Org. Prep. Proced. Int. 1995, 27, 35. Joshi, K. C.; Jain, R.; Dandia, A. J. Fluorine Chem. 1992, 56, 1.
2. Reviews on fluorine-containing heterocycles: Burger, K.; Wucherpfenning, U.; Brunner, E. In Advances in Heterocyclic Chemistry Vol. 60; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Silvester, M. J. In Advances in Heterocyclic Chemistry Vol. 59; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Elguero, J.; Fruchier, A.; Jagerovic, N.; Werner, A. Org. Prep. Proced. Int. 1995, 27, 35. Joshi, K. C.; Jain, R.; Dandia, A. J. Fluorine Chem. 1992, 56, 1.
3. Reviews on fluorine-containing heterocycles: Burger, K.; Wucherpfenning, U.; Brunner, E. In Advances in Heterocyclic Chemistry Vol. 60; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Silvester, M. J. In Advances in Heterocyclic Chemistry Vol. 59; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Elguero, J.; Fruchier, A.; Jagerovic, N.; Werner, A. Org. Prep. Proced. Int. 1995, 27, 35. Joshi, K. C.; Jain, R.; Dandia, A. J. Fluorine Chem. 1992, 56, 1.
4. Reviews on fluorine-containing heterocycles: Burger, K.; Wucherpfenning, U.; Brunner, E. In Advances in Heterocyclic Chemistry Vol. 60; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Silvester, M. J. In Advances in Heterocyclic Chemistry Vol. 59; Katritzky, A. R., Ed.; Academic: San Diego, 1994; p 1. Elguero, J.; Fruchier, A.; Jagerovic, N.; Werner, A. Org. Prep. Proced. Int. 1995, 27, 35. Joshi, K. C.; Jain, R.; Dandia, A. J. Fluorine Chem. 1992, 56, 1.
5. Takahashi, M.; Chigira, K. J. Heterocycl. Chem. 1995, 32, 207. Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. Takahashi, M.; Kotajima, K. Synlett 1990, 353.
6. Takahashi, M.; Chigira, K. J. Heterocycl. Chem. 1995, 32, 207. Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. Takahashi, M.; Kotajima, K. Synlett 1990, 353.
7. Takahashi, M.; Chigira, K. J. Heterocycl. Chem. 1995, 32, 207. Takahashi, M.; Kotashima, H.; Saitoh, T. Heterocycles 1993, 35, 909. Takahashi, M.; Kotajima, K. Synlett 1990, 353.
8. Reviews on sulfonyl carbanions: Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: Oxford, 1993. Thompson, C. M.; Green, D. L. C. Tetrahedron 1991, 47, 4223. Field, L. Synthesis 1978, 713.
9. Reviews on sulfonyl carbanions: Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: Oxford, 1993. Thompson, C. M.; Green, D. L. C. Tetrahedron 1991, 47, 4223. Field, L. Synthesis 1978, 713.
10. Reviews on sulfonyl carbanions: Simpkins, N. S. Sulphones in Organic Synthesis; Pergamon: Oxford, 1993. Thompson, C. M.; Green, D. L. C. Tetrahedron 1991, 47, 4223. Field, L. Synthesis 1978, 713.
11. Thompson, M. E. J. Org. Chem. 1984, 49, 1700.
12. Grunder-Klotz, E.; Humbert, P.; Ehrhardt, J. Heterocycles 1993, 36, 733.
13. Thompson, M. E. Synthesis 1988, 733.
14. Beam, C. F.; Reames, D. C.; Harris, C. E.; Dasher, L. W.; Hollinger, W. M.; Shealy, N. L.; Sandifer, R. M. J. Org. Chem. 1975, 40, 514.
15. Martin, G. In Supplement S: The Chemistry of Sulfur-Containing Functional Groups, Patai, S.; Rappoport, Z., Ed.; Wiley: Chichester, 1993, p 395.
16. Sheehan, J. C.; Zoller, U.; Ben-Ishai, D. J. Org. Chem. 1974, 39, 1817. Bordwell, F. G.; Cooper, G. D. J. Am. Chem. Soc. 1951, 73, 5187.
17. Sheehan, J. C.; Zoller, U.; Ben-Ishai, D. J. Org. Chem. 1974, 39, 1817. Bordwell, F. G.; Cooper, G. D. J. Am. Chem. Soc. 1951, 73, 5187.
18. Müller, P.; Phuong, N. M. Helv. Chim. Acta 1979, 62, 494.
19. The compounds 1a (mp 46-48 °C) and 1 b (mp 68-69 °C) were prepared according to the literature: Nickson, A. J. Am. Chem. Soc. 1964, 86, 1152.