Elena K. Avakyan

Direct oxidative SNH amidation of 1,3,7-triazapyrene

6-Acylamino-1,3,7-triazapyrenes have been synthesized for the first time by direct oxidative nucleophilic substitution of hydrogen.

Amides of 1,3,7-triazapyrene series: synthesis by nucleophilic substitution of alkoxy groups

The treatment of 6,8-dialkoxy-1,3,7-triazapyrenes with sodium acylamides in DMSO at room temperature resulted in ipso substitution of one alkoxy group with amide group, giving 8-acylamino-6-alkoxy-1,3,7-triazapyrenes. The reaction at 65–70°C proceeded as a tandem SNAripso–SN2 process, leading to the formation of 8-acylamino-6-oxo-6,7-dihydro-1,3,7-triazapyrenes.

Oxidative SNH amidation of acridine and tautomerism of N-(acridin-9-yl)benzamides

Direct oxidative nucleophilic substitution of hydrogen atom in acridine molecule was used to synthesize 9-acylaminoacridines. The prototropic amine-imine tautomerism of these compounds was studied.

Urea in an aminodemethoxylation reaction of 6-methoxy-1,3,7-triazapyrenes

Upon reaction of N-anion of urea with 6-methoxy-1,3,7-triazapyrenes in DMSO at room temperature the products of nucleophilic ipso substitution of methoxy group with amino group form in high yields.

Synthesis of Amides by Nucleophilic Substitution of Hydrogen in 3-Nitropyridine

Abstract3-Nitropyridine reacted with nitrogen-centered carboxylic acid amide anions in anhydrous DMSO in the presence of K3Fe(CN)6 via oxidative nucleophilic substitution of hydrogen to give previously unknown N-(5-nitropyridin-2-yl) carboxamides. The reaction of nitrobenzene with urea anion in DMSO enabled one-pot synthesis of bis(4-nitrophenyl)amine.

S N H Alkyl carbamoyl amination of 3-nitropyridine: competitive synthesis of nitro- and nitrosopyridine derivatives

A method has been developed for oxidative SNH alkyl carbamoyl amination of 3-nitropyridine in anhydrous DMSO. When anions of alkyl- and 1,1-dialkylureas were used as nucleophiles, an unusual formation of a mixture consisting of 1-alkyl(1,1-dialkyl)-3-(5-nitropyridin-2-yl)ureas and their nitroso analogs occurred, which was the first such observation with 3-nitropyridine. Only the nitro products formed in the presence of nitrobenzene. Additionally, a range of N-oxides were obtained on the basis of the synthesized compounds.