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Paper | Regular issue | Vol 68, No. 12, 2006, pp.2483-2498
Published online, 24th October, 2006
DOI: 10.3987/COM-06-10862
■ Synthetic Utilization of Polynitro Aromatic Compounds. 5. Multi-Centered Reactivity Pattern in Reactions of 4,6-Dinitro-1,2-benzisothiazoles and -isothiazol-3(2H)-ones with C-, N-, O-, S-, and F-Nucleophiles

Sergei G. Zlotin,* Pavel G. Kislitsin, Fedor A. Kucherov, Evgeny A. Serebryakov, Yury A. Strelenko, and Andrei A. Gakh*

*Oak Ridge Naitonal Laboratory, 1 Bethel Valley Rd., Oak Ridge, TN 37831-6242, U.S.A.

Abstract

Reactions of 4,6-dinitro-1,2-benzisothiazoles, -isothiazol-3(2H)-ones, and -isothiazol-3(2H)-one-1-oxides with C-, N-, O-, S-, and F-nucleophiles give products of aromatic nucleophilic substitution of one or two nitro groups, “vicarious” substitution of the hydrogen atom H-7, or heterocyclic S-N bond cleavage depending on the structure of the starting compound and the nature of the nucleophile. These reactions provide a new synthetic approach to a family of biologically active benzisothiazol-3(2H)-ones based on 2,4,6-trinitrotoluene (TNT).