Selective Synthesis of 1,2-Benzisothiazol-3-one-1-Oxide Nitro Derivatives

Abstract

A new selective synthesis of 1,2-benzisothiazol-3-one-1-oxide nitro derivatives by reaction of 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in wet CH₂Cl₂ has been developed. Reactions of N-unsubstituted 2-benzylthio-4-nitro- and 2-benzylthio-4,6-dinitrobenzamides with gaseous chlorine in 60% AcOH give, instead of the S-oxides, the appropriate 1,2-benzisothiazol-3-one-1,1-dioxide nitro derivatives.

polynitrobenzamides - chlorine - 1,2-benzisothiazole-3-one-1-oxides - 1,2-benzisothiazole-3-one-1,1-dioxides

References

1a Dunlap RP, Boaz NW, Mura AJ, Hlasta DJ, Saindane MT, Court JJ, and Bell MR. inventors; Eur. Pat. Appl. E.P.  594 257. 

2 Subramanayam C. Bell MR. Carabates P. Court JJ. Dority JA. Ferguson E. Gordon R. Hlasta DJ. Kumar V. J. Med. Chem.  1994,  37:  2623 

3a Dunlap RP, Boaz NW, Mura AJ, Kumar V, Subramanayam C, Desai RC, Hlasta DJ, Saindane MT, and Bell MR. inventors; US Patent  5 512 589. 

4a Desai RC, Court JJ, and Hlasta DJ. inventors; US Patent  5 296 496. 

5a Hlasta DJ, Desai RC, Subramanayam C, Court JJ, Bell MR, Kumar V, Dunlap RP, and Latimer LH. inventors; Eur. Pat. Appl. E.P.  550111. 

6 Shui-Lung H. Swern D. J. Org. Chem.  1979,  44:  2510 

7a Zlotin SG. Kislitsin PG. Podgursky AJ. Samet AV. Semenov VV. J. Org. Chem.  2000,  65:  8439 

7b Zlotin SG. Kislitsin PG. Samet AV. Serebryakov EA. Konyushkin LD. Semenov VV. J. Org. Chem.  2000,  65:  8430 

8a Drabowicz J. Midura W. Mikolayczyk M. Synthesis  1979,  39 

8b Levchenko ES. Dubinina TN. Zh. Org. Chim. USSR  1978,  14:  862 

8c Ali MH. Bohnert GY. Synthesis  1998,  1238 

8d Haake M. Gebbing H. Benack H. Synthesis  1979,  97 

8e Harville R. Reed SF. J. Org. Chem.  1968,  33:  3976 

9 Gerasyuto AJ. Zlotin SG. Semenov VV. Synthesis  2001,  300 

10a Wright SW. Abelman MM. Bostrom LL. Corbett RL. Tetrahedron Lett.  1992,  33:  153 

10b Wright SW. Petraitis J. Abelman MM. Batt DG. Bostrom LL. Corbett RL. Decico CP. DiMeo SV. Freimark B. Giannaras JV. Green AM. Jettler JM. Nelson DJ. Orwatt MJ. Pinto PJ. Pretta MA. Sherk SR. Williams JM. Magolde RL. Arner ES. J. Med. Chem.  1994,  37:  3071 

11 Kharasch N. Lagford RB. J. Org. Chem.  1963,  28:  1903 

12a Gibbert EE. Synthesis  1969,  3 

12b Gibbert EE. Sulfonation and Related Reactions   Wiley-Interscience; New York: 1965. 

12c Grosset JS. Langler RF. Canad. J. Chem.  1977,  55:  407 

13 Dippy JFJ. Hawkins BD. Smith BV. J. Chem. Soc.  1964,  154 

14a Roshkov VV. Kuvshinov AM. Gulevskaya VI. Cherin II. Shevelev SA. Synthesis  1999,  2065 

14b Kuvshinov AM. Gulevskaya VI. Roshkov VV. Shevelev SA. Synthesis  2000,  1474 

14c

Samet, A. V.; Zakharov, E. P.; Semenov, V. V.; Buchanan III, A. C.; Gakh, A. A. Synth. Commun. 2001, in press.