STRUCTURE AND TAUTOMERISM OF 1,6-DIALKYLSUBSTITUTED 1,3,4,6-TETRAOXOSYSTEMS AND CLOSEST AZO ANALOGUES THEREOF (REVIEW)

Mukovoz Petr Petrovich, Candidate of chemical sciences, leading researcher, Institute of cell and intracellular symbiosis, Ural branch of the Russian Academy of Sciences
(11 Pionerskaya street, Orenburg, Russia), mpp27@mail.ru
Tarasova Viktoriya Alekseevna, Expert, department of pharmaceutical activity administration, Ministry of Health, Orenburg region (33 Tereshkovoy street, Orenburg); postgraduate student, Orenburg State University
(13 Pobedy avenue, Orenburg, Russia), rianna@bk.ru
Karmanova Ol'ga Gennad'evna, Postgraduate student, Perm State Pedagogical University
(24 Sibirskaya street, Perm, Russia), o_karmanova@mail.ru
Koz'minykh Vladislav Olegovich, Doctor of chemical sciences, professor, head of sub-department of chemistry, Perm State Pedagogical University, (24 Sibirskaya street, Perm, Russia), kvoncstu@yahoo.com

547.341+547.725

Background. 1,3,4,6-Tetracarbonyl compounds and their derivatives differ by structure diversity, high reactivity and prove to be suitable structural blocks in the synthesis of various heterocyclic compounds. Tetraoxosystems, having alkyl substitutes in acyl links, remained scarcely researched before our study. The study aims at supplementing with our data and generalizing the known facts about the structureof 1,6-dialkylsubstituted 1,3,4,6-tetraketones and their nitrogenous heterocyclic derivatives.
Materials and methods. We used atylmethylketones, oxalic ester, sodium methoxide and inert atmosphere of diethyl ether or tetrahydrofuran as the original compounds to obtain 1,6-dialkyl-1,3,4,6-tetraones. As a method of 1,6-dial¬kyl-1,3,4,6-tetraones obtainment the authors used complex ether Claisen condensation of alkylmethylketones with diethyl oxalate in presence of sodium methoxide.
Results. The researchers developed a two-stage method of obtainment of 1,6-dialkyl-1,3,4,6-tetraones with various alkyl substitutes in acyl links by means of sequential interaction of various atylmethylketoneswith diethyl oxalate in presence of sodium methoxide. The authors studied the features of 1,6-dialkyl-1,3,4,6-tetraones structure, discovered previously unknown tautomeric forms. The scientists examined the reactions of 1,6-dialkyl-1,3,4,6-tetraones with N,N- and О,N-binucleofiles and obtained new heterocyclic azine derivatives of 1,6-dialkyl-1,3,4,6-tetraones.
Conclusions. It is deduced that 1,6-dialkyl-1,3,4,6-tetraones in solid state and solutions of nonpolar solvents are presented in bis-chelate dienol form, and in polar solvents there is present (acetone) or prevails (dimethyl sulfoxide) a cyclic oxofuran form.
It is proved that with 1,2-diaminobenzene the 1,6-dialkyl-1,3,4,6-tetraones form heterocyclic azo derivatives.

1,3,4,6-Tetracarbonyl compounds, 1,6-dialkyl-1,3,4,6-tetraones, quinoxaline.

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