309272-28-4Relevant academic research and scientific papers
Synthesis of 2,3-dihydrobenzothiazol-1,1-dioxide and 2,3-dihydro-1,4-benzothiazin-3-one nitroderivatives from 2,4-di- and 2,4,6-trinitrobenzamides
Gerasyuto,Zlotin,Semenov
, p. 300 - 304 (2007/10/03)
Synthetic methods for the conversion of readily available 2,4-di- and 2,4,6-trinitrobenzamides to the previously unknown 2,3-dihydrobenzothiazol-1,1-dioxide, 2,3-dihydro- 1,4-benzothiazin-3-one, and 2,3-dihydro-1,4-benzothiazin-3-one-1,1-dioxide nitroderivatives have been developed. The methods involve selective nucleophilic substitution of an ortho-nitrogroup in polynitrobenzamides by benzylthio or methoxycarbonylmethylthio group followed by oxidation of sulfur atom with hydrogen peroxide and transformation of the amido group to the methoxycarbonylamino group by reaction with diacetoxyiodobenzene in methanol under non-basic conditions. Cyclization of the resulting compounds under the action of diacetoxyiodobenzene or sodium methoxide leads to the 2,3-dihydrobenzothiazole and 2,3-dihydro-1,4-benzothiazin-3one derivatives, respectively.
Synthetic utilization of polynitroaromatic compounds. 1. S-derivatization of 1-substituted 2,4,6-trinitrobenzenes with thiols
Zlotin,Kislitsin,Samet,Serebryakov,Konyushkin,Semenov,Buchanan III,Gakh
, p. 8430 - 8438 (2007/10/03)
Reactions of 1-R-2,4,6-trinitrobenenes (R = alkyl, protected aldehyde, aminocarbonyl, cyano groups, or isoxazole ring) with thiol salts were investigated. In most cases, these reactions gave a mixture of minor para and major ortho substitution products. Reactions of N,N-disubstituted 2,4,6-trinitrobenzamides with S-,O-, and N-nucleophiles afforded products of substitution of the p-nitro group exclusively. 1-Cyano-2,4,6-trinitrobenzene was found to be the most reactive and the least selective: all three nitro groups can be substituted using an excess of thiol salts. 2-R-4,6-dinitrobenzamides showed no regioselectivity under similar conditions to yield 1:1 mixtures of para and ortho isomers.
