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

Evgeny A. Serebryakov; Pavel G. Kislitsin; Victor V. Semenov; Sergey G. Zlotin

doi:10.1055/s-2001-16764

PAPER

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

Evgeny A. Serebryakov, Pavel G. Kislitsin, Victor V. Semenov, Sergey G. Zlotin*
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospekt, 47, 119991, Moscow, Russia
Fax: +7(095)1355328; e-Mail: zlotin@cacr.ioc.ac.ru;

Abstract

All articles of this category

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.

Key words

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

Full Text

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.