Ivan V. Kulakov

Synthesis of 3-Aminopyridin-2(1H)-Ones and 1H-Pyrido[2,3-b][1,4]Oxazin-2(3H)-Ones

The interaction of 1,3-diketones with chloroacetamide produced N-(3-oxoalkenyl)chloroacetamides. Heating of N-(3-oxoalkenyl)chloroacetamides with an excess of pyridine in ethanol or butanol led to the formation of pyridin-2(1Н)-ones, substituted with a pyridine ring at position 3. The reactions of these compounds with hydrazine hydrate produced 3-aminopyridin-2(1Н)-ones. The synthesis of 1H-pyrido[2,3-b][1, 4]oxazin-2(3H)-ones was accomplished by a reaction of 3-aminopyridin-2(1Н)-ones with chloroacetyl chloride.

Synthesis, Structure, and Antiradical Activity of New Methano[1,3]Thiazolo[2,3-d][1,3,5]Benzoxa-Diazocine Derivatives

The reaction of 2,6-methano[1, 3, 5]benzoxadiazocines, obtained in Biginelli reaction, with chloroacetic acid derivatives produced previously unknown tricyclic methano[1,3]thiazolo[2,3-d][1,3,5]benz-oxadiazocines, the structure of which was proved by 1Н NMR spectroscopy and X-ray structural analysis. The methano[1,3]thiazolo[2,3-d][1,3,5]benzoxadiazocines showed no antiradical activity in contrast to the starting 2,6-methano[1,3,5]benzoxadiazocines.

Synthesis and antiradical activity of 4-aryl(hetaryl)-substituted 3-aminopyridin-2(1Н)-ones

The reaction of aryl(hetaryl)-substituted 1,3-diketones with chloroacetamide gave the respective N-(3-oxoalkenyl)chloroacetamides, which were converted to 3-pyridinium-substituted pyridin-2(1Н)-ones upon heating with excess of pyridine in n-butanol. The decomposition of pyridinium salts with hydrazine hydrate resulted in new 4-aryl(hetaryl)-substituted 3-aminopyridin-2(1Н)-ones, which showed strong antiradical activity with respect to ABTS and DPPH radicals.

Synthesis and structure of novel ylidene derivatives of methanobenzo[g]thiazolo[2,3-d][1,3,5]oxadiazocine

Novel benzylidene and furylidene derivatives of tricyclic thiazolo[2,3-d][1,3,5]oxadiazocines were synthesized, and their structures were confirmed by 1H and 13C NMR spectroscopy. It was shown that ylidene derivatives of 11H-5,11,5-pentane-[1,1,5]triyl[1,3]thiazolo[2,3-d]-[1,3,5]oxadiazocin-1-one are obtained as a mixture of Z- and E-isomers. Recrystallization of the isomer mixture affords the major Z-isomer, structure of which has been established by X-ray structural analysis.

Reaction of N -(3-oxoalkenyl)chloroacetamides with sodium p- toluenesulfinate – synthesis of 3-tosylpyridin-2(1 Н )-ones

A series of N-(3-oxoalkenyl)chloroacetamides was prepared by acylation of β-enaminoketones with chloroacetyl chloride. A reaction of these compounds with sodium p-toluenesulfinate in dimethylformamide in the presence of potassium carbonate led to 3-tosylpyridin-2(1H)-ones. The limitations of this reaction were studied.