title: Synthetic utilization of polynitroaromatic compounds. 2. Synthesis Of 4,6-dinitro-1,2-benzisothiazol-3-ones and 4,6-dinitro-1, 2-benzisothiazoles from 2-benzylthio-4,6-dinitrobenzamides.
abstract: Cyclization of 2-benzylthio-4,6-dinitrobenzamides to 4,6-dinitro-1, 2-benzisothiazol-3-ones was achieved using SO(2)Cl(2) in CH(2)Cl(2) at room temperature. Alkylation of these heterocycles proceeded in a nonregioselective manner to yield a mixture of corresponding O- and N-alkylated products. Oxidation of 4,6-dinitro-1,2-benzisothiazoles (50% H(2)O(2) in AcOH) afforded the corresponding S-oxides and S, S-dioxides, depending on oxidation conditions. Unexpectedly, oxidation of a 3-methoxy derivative resulted in ring opening with the formation of the corresponding sulfamide. Chlorination of these 4,6-dinitro-1,2-benzisothiazol-3-ones (PCl(5)-POCl(3)) gave the expected 3-chloroisothiazoles.
authors: Chemical and Analytical Sciences Division, Oak Ridge National Laboratory, Oak Ridge, Tennessee 37831-6197, USA.
authors: S G
authors: SG
authors: Zlotin
authors: P G
authors: PG
authors: Kislitsin
authors: A I
authors: AI
authors: Podgursky
authors: A V
authors: AV
authors: Samet
authors: V V
authors: VV
authors: Semenov
authors: A C
authors: AC
authors: Buchanan III
authors: A A
authors: AA
authors: Gakh