Jerzy Suwiński

Synthesis of 4-Arylaminoquinazolines and 2-Aryl-4-arylaminoquinazolines from 2-Aminobenzonitrile, Anilines and Formic Acid or Benzaldehydes

Abstract 2-Aminobenzonitrile treated with anilines in the presence of aluminium chloride gave respective 2-amino-N-arylbenzamidines. 4-Arylaminoquinazolines lacking a substituent at the 2 position were obtained directly by heating 2-amino-N-arylbenzamidines in formic acid; in similar conditions other carboxylic acids did not react with the amidines. The latter when treated with aldehydes afforded 2-aryl-4-arylimino-1H-2,3-dihydroquinazolines readily oxidizable by potassium permanganate to 2-aryl-4-arylaminoquinazolines.

Synthesis of 4-arylaminoquinazolines via 2-amino-N-arylbenzamidines

Abstract A new synthesis of twelve 4-arylaminoquinazolines from 2-amino- N -arylbenzamidines and formic acid is described. The entering amidines were obtained in the reaction of anthranilonitrile with 50% molar excess of aromatic amines and anhydrous aluminium chloride.

Nitroimidazoles XVII. Nucleophilic amination or ring transformation in reactions of 1-aryl-4-nitroimidazoles with 4-amino-1,2,4-triazole or hydroxylamine

Abstract 1-aryl-4-nitroimidazoles under action of 4-amino-1,2,4-triazole in the presence of MeONa in DMSO undergo a vicarious nucleophilic substitution of hydrogen to give 5-amino-1-aryl-4-nitroimidazoles. If reacted with hydroxylamine in the presence of KOH or MeONa in methanol (but not in DMSO) 1-aryl-4-nitroimidazoles undergo a transformation to 4-acylamino-2-aryl-1-oxy-2H-1,2,3-triazoles but do not yield amination products.

SYNTHESIS OF 1-(2-HYDROXY-3-METHOXYPROPYL)URACILS AND THEIR ACTIVITY AGAINST L1210 AND MACROPHAGE RAW 264.7 CELLS

ABSTRACT The title compounds were obtained from appropriate 5-substituted uracil derivatives and 1,2-oxy-3-methoxypropane in the presence of sodium hydride. Under similar conditions 5-iodouracil gave 2-methoxymethyl-2,3-dihydro-oxazolo[3,2-c]pyrimidine-5,7-dione as a result of intramolecular cine type nucleophilic substitution. Cytotoxicity of 1-(2-hydroxy-3-methoxypropyl)-5-substituted uracil derivatives against L1210 and macrophage RAW 264.7 cells in vitro was examined.

Reduction of aromatic nitrocompounds by sodium borohydride in methanol in the presence of sodium methoxide

Abstract The paper presents the results of the reduction of 4-nitroimidazoles, 4-nitropyrazoles and 3-nitropyridines by sodium borohydride or sodium borodeuteride in methanol in the presence of sodium methoxide, 1-Substituted 4-nitroimidazoles yield oximes of 4-imidazolidinones, the nitropyrazoles and nitropyridines yield respective azoxy compounds. The reaction mechanism proposed in the work makes allowances for catalytic effect of the system methanol-methoxide.

Transformation of 5,5-diaryl-4,5-dihydro-1,2,4-oxadiazoles to 4-arylquinazolines

The transformation of 5,5-diaryl-4,5-dihydro-1,2,4-oxadiazoles to 4-arylquinazolines in boiling acetic anhydride via acyclic 1-acetyloxy-4-aryl-1,3-diaza-1,3-butadienes is described.

Reactions of 1-arenesulfonyl-4-nitroimidazoles with aniline in aqueous methanol solution

Abstract Several 1-arenesulfonyl-4-nitroimidazoles were obtained and reacted with aniline in methanol-water medium at 65–70°C to yield mixtures of 1-arenesulfonylamide. 1-arenesulfonyl-anilide. 4-nitro-1-phenylimidazole and 4(5)-nitroimidazole in varied proportions depending on the arenesulfonyl group.

Synthesis and photochemical behaviour of 4-nitroimidazoles in the presence of oxygen

Abstract Synthesis and photochemical properties of 1-aryl-4-nitroimidazoles are described. These compounds are good sensitizers of superoxide ion. Only 1-phenyl-2-methyl-4-nitroimidazole is a photosensitizer of singlet oxygen.

Nucleophilic amination and ring transformation in 2-methyl-4-nitro-1-phenylimidazole

Abstract 2-methyl-4-nitro-1-phenylimidazole undergoes a nucleophilic substitution of hydrogen in reaction with 4-amino-1,2,4-triazole in the presence of MeONa in DMSO yielding 5-amino-2-methyl-4-nitro-1-phenylimidazole, whereas in reaction with hydroxylamine in the presence of KOH in methanol undergoes a transformation to 4-acetylamino-1-oxy-2-phenyl-2H-1,2,3-triazole. A structure of the latter compound was confirmed by X-ray analysis.

Synthesis of methyl esters of (2s or 2r) 2-(4-nitro-1-imiazolyl) alkanecarboxylic acids

Abstract 1,4-Dinitroimidazole (or its 2-methyl derivative) reacts with chiral a-amino esters and yields chiral esters of of 2-(4-nitro-1-imidazolyl)alkanecarboxylic acids.