RESUMO
The reaction of nitrobenzylic carbanions with dimethyldioxirane (DMD) results in oxidation at the carbanion center or at the nitronate center to give nitrobenzylic carbinols or quinomethanes, respectively. Minor amounts of the methylation products are also formed. Both of these processes were observed for carbanions of (p-nitroaryl)diarylmethanes. The outcome of the oxidation process is very sensitive to the reaction conditions.
RESUMO
The mechanism of the novel dimethyldioxirane (DMD) oxidation of sigma(H) adducts (Meisenheimer complexes) generated from nitroarenes and carbanions was elucidated. The proposed mechanism, which is akin to that of the oxidative Nef reaction, is supported by the isolation of the cyclohexadienone intermediate and the lack of a primary kinetic isotopic effect. Protic solvents (H(2)O, MeOH) enhance the reactivity of DMD through intermolecular hydrogen bonding.
RESUMO
A series of new S-phenylthioglycolic acid derivatives was synthetized via common transformations of alkylated S-phenyl-thioglycolonitrile. The compounds were submitted to pharmacological screening. N,N-Diethylaminoethyl ester of 1-S-phenylcyclopentane carboxylic acid was submitted to detailed studies and showed high local anesthetic properties.
Assuntos
Anestésicos Locais/síntese química , Tioglicolatos/síntese química , Animais , Anti-Inflamatórios , Bile/metabolismo , Blefaroptose , Pressão Sanguínea/efeitos dos fármacos , Gatos , Fenômenos Químicos , Química , Feminino , Motilidade Gastrointestinal/efeitos dos fármacos , Cobaias , Frequência Cardíaca/efeitos dos fármacos , Indicadores e Reagentes , Masculino , Camundongos , Camundongos Endogâmicos , Fisostigmina/antagonistas & inibidores , Ratos , Ratos Endogâmicos , Reserpina/farmacologia , Convulsões/fisiopatologia , Relação Estrutura-Atividade , Tioglicolatos/farmacologia , Tioglicolatos/toxicidadeRESUMO
A series of 13 new 1,1-diphenylacetic acid derivatives was synthesized via common transformations of 2-phenyl-2-(p-nitrophenyl) propio- and butyronitriles. The compounds were submitted to pharmacological screening. 2-Phenyl-2-(p-aminophenyl)propionamide (VIII) showed high anticonvulsant activity.
