- Reaction of N-acetyl- and N-[1-(arylsulfonylimino)ethyl]-1,4-benzoquinone imines with sodium arenesulfinates
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N-Acetyl- and N-[1-(arylsulfonylimino)ethyl]-1,4-benzoquinone imines having no substituent in the 2- and/or 6-position of the quinoid ring react with sodium arenesulfinates preferentially according to the 1,4-addition pattern. The presence of an ArSO
- Konovalova,Avdeenko,Pirozhenko,Ledeneva,Santalova
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p. 1283 - 1291
(2015/01/09)
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- Thiocyanation of N-aryl, N-acetyl, and N-[arylsulfonylimino(methyl)methyl] derivatives of 1,4-benzoquinone monoimine
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N-[arylsulfonylimino(methyl)methyl] derivatives of 1,4-benzoquinone monoimine with alkyl substituents in the quinoid ring have been synthesized and their spectral characteristics were determined. The thiocyanation of N-aryl, N-acetyl, and N-[arylsulfonyli
- Konovalova,Avdeenko,Ledeneva,Yusina,Pirozhenko,Shishkin,Palamarchuk
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p. 635 - 646
(2014/07/08)
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- Activated sterically strained C=N bond in N-substituted p-quinone mono- and diimines: XIV. Reaction of some 3,5-dimethyl-1,4-benzoquinone monoimines with alcohols
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Steric strain in the C=N-C fragment in 3,5-disubstituted N-acyl-1,4-benzoquinone monoimines, unlike their N-arylsulfonyl analogs, leads to increase of the C=N-C angle above 130 or twisting of the double C=N bond and loss of planarity of the quinoid ring.
- Avdeenko,Konovalova,Vasil'Eva,Palamarchuk,Baumer,Shishkin
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- Studies on the mechanism of toxicity of acetaminophen. Synthesis and reactions of N-acetyl-2,6-dimethyl- and N-acetyl-3,5-dimethyl-p-benzoquinone imines
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N-Acetyl-2,6-dimethyl-p-benzoquinone imine and N-acetyl-3,5-dimethyl-p-benzoquinone imine were prepared from 2,6-dimethylacetaminophen and 3,5-dimethylacetaminophen by oxidation with lead tetraacetate. Reaction of N-acetyl-2,6-dimethyl-p-benzoquinone imine with hydrochloric acid gave 3'-chloro-2',6'-dimethyl-4'-hydroxyacetanilide, whereas ethanethiol, aniline, and ethanol gave tetrahedral adducts resulting from addition to the imine carbon. Water gave 2,6-dimethyl-p-benzoquinone. With N-acetyl-3,5-dimethyl-p-benzoquinone imine, water and aniline gave substitution on the imine carbon, yielding 2,6-dimethyl-p-benzoquinone and 3,5-dimethyl-N-phenyl-p-benzoquinone imine, respectively. Ethanethiol gave 3',5'-dimethyl-2'-(ethylthio)-4'-hydroxyacetanilide. The toxicity of 2,6-dimethylacetaminophen and 3,5-dimethylacetaminophen was examined histologically in mice and rats. 3,5-Dimethylacetaminophen was slightly more nephrotoxic but showed a similar hepatotoxicity to acetaminophen. 2,6-Dimethylacetaminophen, like N-methylacetaminophen, showed very little tissue damage.
- Fernando,Calder,Ham
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p. 1153 - 1158
(2007/10/02)
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