New synthetic method to 1,2-benzisothiazoline-3-one-1,1- dioxides and 1,2-benzisothiazoline-3-one-1-oxides from N-alkyl(o- methyl)arenesulfonamides

Tetrahedron

Volumn 55, Issue 52, 1999, Pages 14885-14900

  Katohgi, Masashi ^a   Togo, Hideo ^a   Yamaguchi, Kentaro ^a   Yokoyama, Masataka ^a  

^a CHIBA UNIVERSITY   (Japan)

Author keywords

(diacetoxyiodo)benzene; 1,2 benzisothiazoline 3 one 1 oxide derivatives; 1,2 benzisothiazoline 3 one 1,1 dioxide derivatives

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SACCHARIN DERIVATIVE; SULFONAMIDE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; IRRADIATION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0033601386     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00974-6     Document Type: Article

References (71)

1. (a)Umemoto, T. Yuki Gosei Kagaku Kyokaishi 1983, 41, 251.
2. (b) Varvoglis, A. Synthesis 1984, 709.
3. (c) Ochiai, M.; Nagao, Y. Yuki Gosei Kagaku Kyokaishi 1986, 44, 660.
4. (d) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431.
5. (e) Moriarty, R. M.; Vaid, R. K.; Koser, G. F. Synlett 1990, 365.
6. (f) Prakash, O.; Saini, N.; Sharma, P. K. Synlett 1994, 221.
7. (g) Kitamura, T Yuki Gosei Kagaku Kyokaishi 1995, 53, 893.
8. (h) Kita, Y.; Takada, T.; Tohma, H. Pure Appl Chem. 1996, 68, 627.
9. (i) Muraki, T.; Togo, H.; Yokoyama, M. Rev. Heteroatom Chem. 1997, 17, 213.
10. (j) Zhdankin, V. V. Rev. Heteroatom Chem. 1997, 17, 133.
11. (a) Concepción, J. I.; Francisco, C. G.; Freire, R.; Hernández, R.; Salazar, J. A.; Suárez, E.; J. Org.Chem. 1986, 51, 402.
12. (b) Singh, R.; Just, G.; Synth. Commun. 1988, 18, 1327.
13. (c) Minisci, F.; Vismara, E.; Fontana, F.; Barbosa, M. C. N. Tetrahedron Lett. 1989, 30, 4569.
14. (d) Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron Lett. 1991, 32, 6559.
15. (e) Togo, H.; Aoki, M.; Yokoyama, M. Chem. Lett. 1991, 1691.
16. (f) Togo, H.; Aoki, M.; Yokoyama, M. Chem. Lett. 1992, 2169.
17. (g) Togo, H.; Aoki, M.; Yokoyama, M. Tetrahedron 1993, 49, 8241.
18. (h) Togo, H.; Aoki, M.; Kuramochi, T.; Yokoyama, M. J. Chem. Soc., Perkin Trans.1 1993, 2417.
19. (i) Togo, H.; Taguchi, R.; Yamaguchi, K.; Yokoyama, M. J. Chem. Soc., Perkin Trans.1 1995, 2135.
20. (j) Togo, H.; Muraki, T.; Yokoyama, M. Synthesis 1995, 155.
21. (a) Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E.; Tetrahedron Lett. 1984, 25, 1953.
22. (b) Francisco, C. G.; Freire, R.; Rodrigues, M. S.; Suárez, E. Tetrahedron Lett. 1987, 28, 3397.
23. (c) Freire, R.; Hernández, R.; Rodrigues, M. S.; Suárez, E. Tetrahedron Lett. 1987, 28, 981.
24. (d) Furuta, K.; Nagata, T.; Yamamoto, H. Tetrahedron Lett. 1988, 29, 2215.
25. (e) Hernández, R.; Marrero, J. J.; Suárez, E. Tetrahedron Lett. 1988, 29, 5982.
26. (f) de Armas, P.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans.1 1989, 405.
27. (g) Brimble, M. A.; Williams, G. M.; Baker, R.; James, M. Tetrahedron Lett. 1990, 31, 3043.
28. (h) Ellwood, C. W.; Pattenden, G. Tetrahedron Lett. 1991, 32, 1591.
29. (i) de Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 72.
30. (j) de Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865.
31. (k) de Armas, P.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1993, 34, 7731.
32. (l) Boto, A.; Betancor, C.; Suárez, E. Tetrahedron Lett. 1994, 35, 5509.
33. (m) Boto, A.; Betancor, C.; Suárez, E. Tetrahedron Lett. 1994, 35, 6993.
34. (n) Arencibia, T.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1994, 35, 7463.
35. (o) Francisco, C. G.; Gonzárez, C. C.; Suárez, E. Tetrahedron Lett. 1996, 37, 1687.
36. (a) de Armas, P.; Carrau, R.; Concepción, J. I.; Francisco, C. G.; Hernández, R.; Suárez, E. Tetrahedron Lett. 1985, 26, 2493.
37. (b) Hernández, R.; Medina, M. C.; Salazar, J. A.; Suárez, E. Tetrahedron Lett. 1987, 28, 2533.
38. (c) Carrau, R.; Hernández, R.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1987, 937.
39. (d) de Armas, P.; Francisco, C. G.; Hernández, R.; Salazar, J. A.; Suárez, E. J. Chem. Soc., Perkin Trans. 1 1988, 3255.
40. (e) Dorta, R. L.; Francisco, C. G.; Suárez, E. J. Chem. Soc., Chem. Commun. 1989, 1168.
41. (a) Kita, Y.; Tohma, H.; Hatanaka, K.; Takada, T.; Fujita, S.; Mitoh, S.; Sakurai, H.; Oka, S. J. Am. Chem. Soc. 1994, 116, 3684.
42. (b) Kita, Y.; Takada, T.; Mihara, S.; Whelan, B. A.; Tohma, H. J. Org. Chem. 1995, 60, 7144.
43. (c) Kita, Y.; Arisawa, M.; Gyoten, M.; Nakajima, M.; Hamada, R.; Tohma, H.; Takada, T. J. Org. Chem. 1998, 63, 6625.
44. (a) Togo, H.; Muraki, T.; Yokoyama, M. Tetrahedron Lett. 1995, 36, 7089.
45. (b) Muraki, T.; Togo, H.; Yokoyama, M. Tetrahedron Lett. 1996, 37, 2441.
46. (c) Togo, H.; Muraki, T.; Hoshina, Y.; Yamaguchi, K.; Yokoyama, M. J. Chem. Soc., Perkin Trans.1 1997, 787.
47. (a) Lombardino, J. G.; Wiseman, E. H.; McLamore, W. M. J. Med. Chem. 1971, 14, 1171.
48. (b) Svahn C. M.; Jönsson, N. Å. Acta Chem. Scand., (B) 1978, 32, 137.
49. (c) Davis, M. "Organic Compounds of Sulfur, Selenium, and Tellurium", vol. 5, Chap 10, Ed by The Chemical Society, London (1979).
50. (d) Pain, D. L.; Peart, B. J.; Wooldridge, K. R. H. "Comprehensive Heterocyclic Chemistry", Eds Katrizky A R.; Rees, C. W., Vol.6, Pergamon Press, Oxford (1984).
51. (e) Drug of the Future, 1986, 11, 565.
52. (f) Sunkel, C. E.; de Casa-Junna, M. F.; Cillero, F. J.; Piego, J. G.; Ortega, M. P. J. Med. Chem. 1988, 31, 1886.
53. (g) Choi, S.-Y.; Lee, S.-G.; Yoon, Y.-J.; Kim, K.-W. J. Heterocyclic Chem. 1989, 26, 1073.
54. (h) Nagasawa, H. T.; Kawle, S. P.; Elberling, J. A.; DeMaster, E. G.; Fukuto, J. M. J. Med. Chem. 1995, 38, 1865.
55. (i) Yeung, K.-S.; Meanwell, N. A.; Tetrahedron Lett. 1998, 39, 5309.
56. (a) Desai, R. C.; Farrell, R. P.; Kuo, G. -H.; Hlasta, D. J. Synlett 1994, 933.
57. (b) Court, J. J.; Lessen, T. A.; Hlasta, D. J. Synlett 1995, 423.
58. (c) Hlasta, D. J.; Subramanyam, C.; Bell, M. R.; Carabateas, P. M.; Court, J. J.; Desai, R. C.; Drozd, M. L.; Eickhoff, W. M.; Ferguson, E. W.; Gordon, R. J.; Johnson, J. A.; Kumar, V.; Maycock, A. L.; Mueller, K. R.; Pagani, E. D.; Robinson, D. T.; Saindane, M. T.; Silver, P. J.; Subramanian, S. J. Med. Chem. 1995, 38, 739.
59. (a) Watanabe, H.; Gay, R. L.; Hauser, C. R J. Org. Chem. 1968, 33, 900.
60. (b) Lombardino, J. G. J. Org. Chem. 1971, 36, 1843.
61. (c) Saari, W. S.; Schwering, J. E. J. Heterocyclic Chem. 1986, 23, 1253.
62. (d) Hlasta, D. J.; Court, J. J.; Desai, R. C. Tetrahedron Lett. 1991, 32, 7179.
63. (e) Desai, R. C.; Hlasta, D. J.; Monsour, G.; Saindane, M. T. J. Org. Chem. 1994, 59, 7161.
64. (f) Yeung, Kap.-S.; Meanwell, N. A.; Li, Y.; Gao, G. Tetrahedron Lett. 1998, 39, 1483.
65. Togo, H.; Hoshina, Y.; Muraki, T.; Nakayama, H.; Yamaguchi, K.; Yokoyama, M. J. Org. Chem. 1998, 63, 5193.
66. As a preliminary report: Togo, H.; Katohgi, M.; Yokoyama, M. Synlett 1998, 131.
67. (a) Klyuev, V. N.; Korzhenevskii, A. B. Khim. Khim. Tekhnol. 1978, 21, 31.
68. (b) Szabo, J.; Szucs, E.; Fodor, L.; Katocs, A.; Bernath, G. Tetrahedron 1988, 44, 2985.
69. (a) Schmeisser, M.; Dahmen, K.; Sartori, P. Chem. Ber. 1967, 100, 1633.
70. (b) Mckillop, A.; Kemp, D. Tetrahedron 1989, 45, 3299.
71. Oae, S.; Togo, H.; Numata, T.; Fujimori, K. Chem. Lett., 1980, 1193.