131941-79-2Relevant academic research and scientific papers
REACTION OF N-ARYLSULFONYL-2-ARENESULFONAMIDO-1,4-BENZOQUINONE 4-IMINES WITH AROMATIC AMINES
Avdeenko, A. P.,Evgrafova, N. I.,Tolmachev, A. A.,Polyakov, A. E.
, p. 1516 - 1521 (2007/10/02)
The reaction of N-arylsulfonyl-2-arenesulfonamido-1,4-benzoquinone 4-imines with aromatic amines leads to N-aryl-2-arenesulfonamido-5-arylamino-1,4-benzoquinone 4-imines.Their structures were proved by alternative syntheses and also by the data from PMR and IR spectroscopy and mass spectrometry.
QUINONE IMINES AND QUINONOID MACROCYCLES XVII. REACTION OF 2-BENZENESULFONAMIDO-N-BENZENESULFONYL-1,4-BENZOQUINONE MONOIMINE WITH PRIMARY AROMATIC AMINES
Markava, E. Ya.,Liepin'sh, E. E.,Freimanis, Ya. F.,Gustinya, D. V.,Leivin'sh, G. M.
, p. 1716 - 1721 (2007/10/02)
In the reaction of 2-benzenesulfonamido-N-benzenesulfonyl-1,2-quinone monoimine with primary aromatic amines in low-polarity media 1,2-addition of the nucleophile to the substrate competes with 6,3-addition.In a polar solvent the equilibrium is displaced toward 6,3-addition and the formation of products from secondary reaction by a formal mechanism of substitution of the sulfonamido group at position 2 of the quinonoid ring.It is supposed that such change in the reactivity of N-arylsulfonyl-1,4-benzoquinone imine is due to the presence of the benzenesulfonamido groupat position 2, which creates the prerequisites for the equilibrium between the ortho- and para-quinone imine structures both in the initial state and in the 6,3-addition products.
