A practical synthesis of N-substituted 1,2-benzisothiazolin-3-ones from N,N′-disubstituted 2,2′-dithiodibenzamides

Synthesis

Volumn , Issue 10, 2004, Pages 1585-1588

  Sano, Tomohumi ^a   Takagi, Toshiyuki ^a   Gama, Yasuo ^a   Shibuya, Isao ^a   Shimizu, Masao ^a  

^a NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

Amides; Benzisothiazoles; Disulfides; Hydroxylamines; Oximes

Indexed keywords

DERIVATIVES; KETONES; NITROGEN; SUBSTITUTION REACTIONS;

ALKYL GROUP;

SYNTHESIS (CHEMICAL);

1,2 BENZISOTHIAZOLE DERIVATIVE; BENZAMIDE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL REACTION; HYDROXYLATION; OXIDATION; SYNTHESIS;

EID: 3142774940     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829101     Document Type: Article

References (23)

1. (a) Davis, M. Adv. Heterocycl. Chem. 1972, 14, 43.
2. (b) Pain, D. L.; Peart, B. J.; Wooldridge, K. R. H. Comprehensive Heterocyclic Chemistry, Vol. 6; Katritzky, A. R.; Rees, C. W.; Potts, K. T., Eds.; Pergamon: Oxford, 1984, 175.
3. (a) Kim, W.; Dannaldson, J.; Gates, K. S. Tetrahedron Lett. 1996, 37, 5337.
4. (b) Etsuzan, T.; Kitagawa, S.; Kamioka, C.; Miki, S. Japan Pat. Appl. JP 20007667, 2000; Chem. Abstr. 2000, 132, 78550.
5. (c) Chiyoda, T.; Iida, K.; Takatori, K.; Kajiwara, M. Synlett 2000, 1427.
6. (d) Jin, C. K.; Moon, J.-K.; Lee, W. S.; Nam, K. S. Synlett 2003, 1967.
7. Shimizu, M.; Kikumoto, H.; Konakahara, T.; Gama, Y.; Shibuya, I. Heterocycles 1999, 51, 3005.
8. Reissert, A.; Manns, E. Ber. Dtsch. Chem. Ges. 1928, 61, 1308.
9. (a) Bartlett, R. G.; McClelland, E. W. J. Chem. Soc. 1934, 818.
10. (b) Kamigata, N.; Hashimoto, S.; Kobayashi, M.; Nakanishi, H. Bull. Chem. Soc. Jpn. 1985, 58, 3131.
11. (c) Okachi, R.; Niino, H.; Kitaura, K.; Mineura, K.; Nakamizo, Y.; Murayama, Y.; Ono, T.; Nakamizo, A. J. Med. Chem. 1985, 28, 1772.
12. (d) Loo, J. A.; Holler, T. P.; Sanchez, J.; Gogliotti, R.; Maloney, L.; Reily, M. D. J. Med. Chem. 1996, 39, 4313.
13. Katz, L.; Schroeder, W. J. Org. Chem. 1954, 19, 103.
14. Turpin, J. A.; Song, Y.; Inman, J. K.; Huang, M.; Wallqvist, A.; Maynard, A.; Covell, D. G.; Rice, W. G.; Appella, E. J. Med. Chem. 1999, 42, 67.
15. Ranganathan, S.; Muraleedharan, K. M.; Bharadwaj, P.; Chatterji, D.; Karle, I. Tetrahedron 2002, 58, 2861.
16. (a) Seko, S.; Kawamura, N. J. Org. Chem. 1996, 61, 442.
17. (b) Seko, S.; Miyake, K.; Kawamura, N. J. Chem. Soc., Perkin Trans. 1 1999, 1437.
18. The stoichiometry of the reaction means that 100% yield corresponds to 2 equiv of 2 produced for 1 equiv of 1.
19. Shimizu, M.; Takeda, A.; Fukazawa, H.; Abe, Y.; Shibuya, I. Heterocycles 2003, 60, 1855.
20. Vitali, T.; Amoretti, L.; Plazzi, V. Farmaco 1968, 23, 1075; Chem. Abstr. 1969, 70, 37701.
21. Vitali, T.; Amoretti, L.; Plazzi, V. Farmaco 1968, 23, 1075; Chem. Abstr. 1969, 70, 37701.
22. Shimizu, M.; Sugano, Y.; Konakahara, T.; Gama, Y.; Shibuya, I. Tetrahedron 2002, 58, 3779.
23. Uchida, Y.; Kozuka, S. Bull. Chem. Soc. Jpn. 1982, 55, 1183.