Kh. S. Shikhaliev

Heterocyclization of quinazol-2-ylguanidines. 1. Reaction with amino acids

Condensation of 6(7)-R-4-methylquinazol-2-ylguanidines with α-amino acids produces 2-hydroxyimidazoles; with anthranilic acid, the corresponding 4-hydroxyquinazolines.

Chemistry of Pyrazole-3(5)-Diazonium Salts (Review)*

The methods of synthesis, structure, reactivity, and synthetic utility of pyrazole-3(5)-diazonium salts are reviewed here for the first time, with emphasis on heterocyclization reactions of these compounds.

The Role of Organic Additives in the Electroless Nickel Plating Bath

Organic additives to electroless plating baths are shown to affect the surface reaction by changing the catalytic activity of the surface. The presence of a thioketone group in the additive increases the surface activity, which results in acceleration of the target reaction. The presence of the iminogroup favors the formation of complexes and alters the rates of concurrent reactions, which weakens the surface activity. The reaction in the volume is governed by the inhibiting properties of additives dependent on the identity of functional groups. The greater the electron-donor properties of the additive, the higher their adsorbability and the stronger the blocking effect, which stabilizes the electrolyte.

Reaction of cyanamides with N,N-binucleophiles

Reactions of 4,6-dimethylpyrimidin-2-yl-and aroylcyanamides with benzene-1,2-diamine, ethylenediamine, cyclohexane-1,2-diamine, and naphthalene-1,8-diamine leads to 1H-benzimidazol-2-amine, imidazolidin-2-imine, perhydrobenzimidazol-2-imine, and 1H-perimidin-2-amine derivatives, respectively.

Three-component condensation of hetarylguanidines with aldehydes (ketones) and dicarbonyl compounds

The three-component condensation of benzoxa(thia)zolylguanidines, aldehydes (ketones), and β-dicarbonyl compounds (acetyl-and benzoylacetone, ethyl acetoacetate, acetoacetanilides, cyclohexanedione-1,3 and its derivatives) has been studied.

Transformations of 3-alkyl-4-(methoxyphenyl)-1H-pyrazole-5-diazonium salts

The coupling of 3-alkyl-4-(methoxyphenyl)-1H-pyrazole-5-diazonium salts with acetylacetone followed by cyclization of the formed heterylhydrazones resulted in pyrazolo[5,1-c][1,2,4]triazines. The 4-(3,4-dimethoxyphenyl)-3-methyl-1H-pyrazole-5-diazonium salt was not involved into a similar reaction but suffered an intramolecular azo coupling giving pyrazolo[3,4-c]-cinnoline.

CONDENSATION OF 5-AMINO-4-ARYLPYRAZOLES WITH ITACONIC ACID AND MALEIC ANHYDRIDE

Substituted 5-amino-4-arylpyrazoles on condensation with itaconic acid form substituted tetrahydropyrazolo[1,5-a]pyrimidines, and on condensation with maleic anhydride form 2,3-dihydro-1H-imidazolo[1,2-b]pyrazoles, which on more extended heating rearrange into tetrahydro-pyrazolo[1,5-a]pyrimidines.

Regioselective and regiospecific reactions of ethyl ortho-(dimethylaminovinylazoloazinylcarboxylates with hydrazine

Selectivity of reactions of ethyl 4-[(E)-2(dimethylamino)vinyl]pyrazolo[5,1-c]-[1,2,4]triazino-3-ylcarboxylates and ethyl 7-[(E)-2-(dimethylamino)vinyl][1,2,4]triazolo[1,5]pyrimidine-6-ylcarboxylates with hydrazine in various solvents was studied. The formation of a pyridone cycle proceeds regiospecifically in dimethyl formamide or dimethyl acetamide. A regioselective cyclization resulting in fused 1,2-diazepines occurs in acetic or propionic acid.

3-aryl(alkyl)quinazoline-2,4(1H,3H)-diones and their alkyl derivatives

Two-stage reaction of methyl anthranilate with aryl(alkyl) isocyanates in keeping with the quantumchemical calculations and XRD analysis resulted in 3-aryl(alkyl)quinazoline-2,4(1H,3H)-diones that by treatment with alkyl halides, phenacyl bromides, esters and amides of chloroacetic acid were converted into the corresponding 1-alkyl derivatives.

2-Quinazolylguanidines in Heterocyclization Reactions. 3. Synthesis of 2-[(6-R-4-Methyl-2-quinazolyl)amino]pyrimidine-(1H)-ones

We synthesized 2-(6-R-4-methyl-2-quinazolyl)amino-1,4-dihydropyrimid-4-ones by reaction of 6-R-4-methyl-2-quinazolylguanidines with acylacetic esters.