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.

No abstract

No abstract

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.

A preparative method for the synthesis of 4,6 dinitroanthranil by intramolecular cycliza tion of 2 azido 4,6 dinitrobenzaldehyde was developed.

No abstract

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 .

No abstract