Conditions were found under which 2,4,6 trinitrostyrene derived from 2,4,6 trinitrotolu ene adds nucleophiles (thiophenol, aniline, and aliphatic amines) at the vinyl fragment to form the corresponding β Х ethyl 2,4,6 trinitrobenzenes (X = PhS, PhNH, or R 2 N). In the reac tions with primary aromatic amines, the initially formed adducts undergo intramolecular replacement of the nitro group followed by aromatization of the indolines that formed to the corresponding N substituted 4,6 dinitroindoles.
The direction of nucleophilic substitution for the nitro group in E 2,4,6 trinitrostilbenes under the action of arene and alkanethiols or phenols in the presence of inorganic bases was studied. Products of o NO 2 group replacement in the presence of PhCH 2 SH were used to obtain earlier unknown 2 aryl 4,6 dinitrobenzo[b]thiophenes and their 3 chloro derivatives. In these fused heterocycles, the 4 NO 2 group can be selectively displaced by a nucleophile.
Reactions of nucleophiles with 3 R 4,6 dinitrobenzo[c]isoxazoles (anthranils) were stud ied. Reactions of 4,6 dinitroanthranil (R = H) with anionic O and S nucleophiles (phenols and benzenethiols in the presence of K 2 CO 3 ) do not result in displacement of the nitro groups. The malonodinitrile anion (C nucleophile) attacks the C(3) atom with opening of the isoxazole ring followed by recyclization into 2 amino 5,7 dinitroquinoline 3 carbonitrile N oxide. The 5 NO 2 group in the latter is smoothly replaced under the action of benzenethiol and 4 chlo rophenol in the presence of K 2 CO 3 . In the case of 3 substituted anthranil (R = COCH 3 ), one nitro group (4 NO 2 ) is replaced under the action of benzenethiol and NaN 3 .
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.