292163-55-4Relevant academic research and scientific papers
Synthetic utilization of polynitroaromatic compounds. 4. Synthesis of nitro-free 4,6-disubstituted 3-aminobenzothiophene derivatives based on 2,4,6-trinitrobenzamide
Zlotin, Sergei G.,Kislitsin, Pavel G.,Kucherov, Fedor A.,Gakh, Andrei A.
, p. 1109 - 1119 (2007/10/03)
A convenient synthesis of nitro-free 4,6-disubstituted 3-aminobenzothiophenes, their S-oxides and S,S-dioxides based on the available 2,4,6-trinitrobenzamide has been developed. The synthesis entails stepwise nucleophilic substitution of all nitro groups in the starting compound by S-, N-, and O-nucleophiles followed by Thorpe-Ziegler cyclization.
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.
