The Preparation of 3-Substituted 1,2-Benzisothiazole 1,1-Dioxides from Lithiated Intermediates or Grignard Reagents and Methyl 2-(Aminosulfonyl)benzoate

Journal of Heterocyclic Chemistry

Volumn 41, Issue 2, 2004, Pages 295-298

  Dunn, S Patrick ^a   Hajiaghamohseni, Laela M ^a   Lioi, Sara B ^a   Meierhoefer, Michelle A ^a   Walters, Matthew J ^a   Beam, Charles F ^a  

^a Department of Teacher Education and Department of Sociology and Anthropology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOLE 1,1 DIOXIDE DERIVATIVE; BENZOIC ACID DERIVATIVE; ISOTHIAZOLE DERIVATIVE; METHYL 2 (AMINOSULFONYL)BENZOATE; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLIZATION; GRIGNARD REACTION; LITHIATION; POLYMERIZATION; PROTON TRANSPORT;

EID: 2342529266     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570410225     Document Type: Article

References (48)

1. [1a] D. W. Brown and M. Sainsbury, Sci. Synth., 11, 573 (2002);
2. [b] A. Siegemund, K. Taubert and B. Schulze, Sulfur Reports, 23, 279 (2002);
3. [c] K. Wojciechowski, Heterocycles, 57, 1717 (2002);
4. [d] B. Schulzeand K. Illgen, J. Prakt. Chem./Chemiker-Zeitung, 339, 1 (1997).
5. [2a] G. Primofiore, F. DaSettimo, C. LaMotta, F. Simorini, A. Minutolo and E. Boldrini, Formaco, 52, 583 (1997);
6. [b] A. Burgos, G. R. Duffin, G. J. Ellames and K. J. Wedge, J. Label. Compds. Radiopharm., 38, 193 (1996);
7. [c] F. A. Davis, C. Clark, A. Kumar and B.-C. Chen, J. Org. Chem., 59, 1184 (1994);
8. [d] T. Podona, B. Guardiola-Lemaitre, D.-H. Caignard, G. Adam, B. Pfeiffer, P. Renard and G. Guillaumet, J. Med. Chem., 37, 1779 (1994).
9. [3a] P. Naumov, O. Jovanovski, M. G. B. Drew and S. W. Ng, Inorg. Chim. Acta, 314, 154 (2001);
10. [b] Y. I. Binev, C. T. Petkov and L. Pejov, Spectrochim. Acta, Part A: Mol. Biomol. Spect., 56A, 1949 (2000);
11. [c] P. Naumov and G. Jovanovski, Spectrochim. Acta, Part A: Mol. Biomol. Spect., 56A, 1305 (2000);
12. [d] L. Pejov, G. Jovanovski, O. Grupce and B. Soptrajanov, J. Mol. Struct., 410-411, 365 (1997);
13. [e] W. Danikiewicz and K. Wojciechowski, Euro. Mass Spectrom., 3, 55 (1997);
14. [f] O. Grupce, M. Penavi and G. Jovanovski, J. Chem. Crystal., 24, 581 (1994).
15. [4a] R. A. Abramovitch, E. M. Smith, M. Humber, B. Purtschert, P. C. Srinivasan, and G. M. Singer, J. Chem. Soc., Perkin Trans. 1, 2589 (1974);
16. [b] F. A. Davis, J. C. Towson, D. B. Vashi, R. Thimma Reddy, J. P. McCauley, Jr., M. E. Harakal and D. J. Gosciniak, J. Org. Chem., 55, 1254 (1990);
17. [c] A. Mustafa and M. K. Hilmy, J. Chem. Soc., 1339 (1952).
18. [5a] B.S. Ismail and T.-V. Chong, J. Oil Palm Res., 13, 1 (2001);
19. [b] R. K. Juhler, S. R. Sorensen, and L. Larsen, Water Res., 35, 1371 (2001);
20. [c] I. Braschi, A. Pusino, C. Gessa and J.-M. Bollag, J. Ag. Food Chem., 48, 2565 (2000);
21. [d] Y. Xi, X. Wang, L. Kong and L. Wang, Pesticide Sci., 55, 751 (1999);
22. [e] L. Wei, H. Yu, Y. Sun, J. Fen and L. Wang, Chemosphere, 37, 747 (1998).
23. [6a] E. Bezemer and S. Rutan, Anal. Chim. Acta, 459, 277 (2002);
24. [b] E. Bezemer and S. Rutan, Anal. Chem., 73, 4403 (2001);
25. [c] R. Bossi, K. Vejrup and C. S. Jacobsen, J. Chromat. A, 855, 575 (1999);
26. [d] W. Winnik, W. Brumley and L. Betowski, J. Mass Spectrom., 30, 1574 (1995).
27. L. Wei, H. Yu, J. Cao, Y. Sun, J. Fen and L. Wang, Chemosphere, 38, 1713 (1999).
28. [8a] Y. Chen and S. McN. Sieburth, Synthesis, 2191 (2002);
29. [b] H. B. Jannet, A. A. Mourabit, A. Gateau-Olesker, C. Marazano and Z. Mighri, Tetrahedron: Asymm., 10, 2381 (1999);
30. [c] B. Lygo, Tetrahedron, 51, 12859 (1995);
31. [d] I. Pevet, C. Meyer and J. Cossy, Tetrahedron Lett., 42, 5215 (2001);
32. [e] Y. Honda, S. Katayama, M. Kojima, T. Suzuki and K. Izawa, Tetrahedron Lett., 44, 3163 (2003);
33. [f] A. K. Banerjee and B. Achari, Tetrahedron Lett., 349 1209 (1993);
34. [g] B. Lygo, Synlett, 764 (1993);
35. [h] M. Yamaguchi, K. Shibato, H. Nakashima and T. Minami, Tetrahedron, 44, 4767 (1988);
36. [i] M. Yamaguchi, K. Shibato and I. Hirao, Chem. Lett., 1145 (1985);
37. [j] S. N. Huckin and L. Weiler, Can. J. Chem., 52, 1343 (1974);
38. [k] S. N. Huckin and L. Weiler, Tetrahedron Lett., 2405 (1972);
39. [l] N. S. Narasimhan and R. K. Ammanamanchi, J. Org. Chem., 48, 3945 (1983).
40. [9a] D. R. Hurst, K. L. French, A. J. Angel, A. R. Williams, M. E. Rampey, T. S. Guion, K. W. Chan, C. M. Kassis, S. L. Studer-Martinez, and C. F. Beam, J. Heterocyclic Chem., 35, 1357 (1998);
41. [b] A. J. Angel, A. E. Finefrock, K. L. French, D. R. Hurst, A. R. Williams, M. E. Rampey, S. L. Studer-Martinez and C. F. Beam, Can. J. Chem., 77, 94 (1999).
42. [10a] J. R. Downs, S. J. Pastine, J. D. Townsend, H. A. Greer, W. Kelley, Jr., D. A. Schady, C. R Metz, C. D. Almquist, W. T. Pennington, R. D. Bailey Walsch, T. A. Lentz McConaughy, and C. F. Beam, J. Heterocyclic Chem., 38, 695 (2001); compound 8 in the report is solvated wih tert-butyl alcohol;
43. [b] S. P. Grant, M. C. Embree, J. R. Downs, J. D. Townsend, C. D. Hornsby and C. F. Beam, Indust. & Eng. Chem. Res., 42, 5721 (2003); see hydrated compound 2f;
44. [c] M. J. Walters, S. P. Dunn, E. Choi, A. N. D'Elia, M. E. Warner, and C. F. Beam, Synth. Commun, 33, 4163 (2003); see hydrated compounds 6, 13, 15, and 16.
45. [11a] R.A. Abramovitch, I. Shinkai, B. J. Mavunkel, K. M. More, S. O'Connor, G. H. Ooi, W. T. Pennington, P. C. Srinivasan and J. R. Stowers, Tetrahedron, 52, 3339 (1996);
46. [b] C. K. F. Hermann, J. A. Campbell, T. D. Greenwood, J. A. Lewisand and J. F. Wolfe, J. Org. Chem., 57, 5328 (1992).
47. R. A. Abramovitch, K. M. More, I. Shinkai, and P. C. Srinivasan, Heterocycles, 5, 95 (1976).
48. D. Hellwinkel, Synthesis, 394 (1989).