RU2282630C1 - Method for synthesis of 1,8-dimethyl-3,6-diazadihomoadamantane-9,10-dione - Google Patents

Abstract

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to a method for synthesis of 1,8-dimethyl-3,6-diazadihomoadmantane-9,10-dione. Compounds of class 3,6-diazadihomoadamantane-9,10-dione possess an antiviral effect comparable with antiviral effect of aminoadamantane, elicit strychnine-like activity and show bactericidal, fungicide and algicidic properties also. Proposed method for preparing 1,8-dimethyl-3,6-diazadihomoadamantane-9,10-dione involves interaction of 1,8-dimethyl-3,6,10,13-tetraazatetracyclo[8,4,1,1^8,130^2,7]hexadeca-2,6-diene with water in the presence of hydrochloric acid and sodium nitrite at room temperature. The parent 1,8-dimethyl-3,6,10,13-tetraazatetracyclo[8,4,1,1^8,130^2,7]hexadeca-2,6-diene is prepared in the condensation reaction of tetramethylenediethylenetetramine and 3,4-hexanedione in the presence of acetic acid in isopropyl alcohol medium at room temperature. Then the reaction mixture is neutralized with potash aqueous solution, water is evaporated under vacuum and solid residue is extracted with heptane. After recrystallization from heptane 1,8-dimethyl-3,5-diazadihomoadamantane-9,10-dione is prepared. The yield of the compound is 78%. Invention provides the development of available method of synthesis of 1,8-dimethyl-3,6-diazadihomoadamantane-9,10-dione.

EFFECT: improved method of synthesis.

1 ex

Description

The invention relates to the field of organic chemistry, and specifically to a method for producing 1,8-dimethyl-3,6-diazadigomoadamantane-9,10-dione, which has the following structure:

Compounds of the class 1,8-dimethyl-3,6-diazadigomoadamantan-9,10-dione have an antiviral effect comparable to the antiviral effect of aminoadamantane, exhibit strychnine-like activity, and also have bactericidal, fungicidal and algicidal properties.

A known method for producing 1-alkyl and 1-aryl-3,6-diazagomoadamantan-9-ones by condensation of tetramethylene diethylenetetramine (TDT) with various monoketones in the presence of acetic acid as a catalyst [Kuznetsov AI, Vladimirova IA, Basargin E.B. and other Heteroadamantanes and their derivatives. II. Synthesis of 3,6-diazagomoadamantan-9-one and its derivatives with substituents in nodal positions // CGS. - 1990. - No. 5. - S.675-680]. However, upon condensation of TDT with α-diketone, namely 3,4-hexanedione, instead of the expected 1,8-dimethyl-3,6-diazadigomoadamantan-9,10-dione, 1,8-dimethyl-3,6,10 was obtained , 13-tetraazatetracyclo [8.4.1.1 ^8.13 0 ^2.7 ] hexadeca-2,6-diene.

The technical task of the invention is the development of an affordable method for the synthesis of 1,8-dimethyl-3,6-diazadigomoadamantane-9,10-dione.

The technical result of the invention is that 1,8-dimethyl-3,6,10,13-tetraazatetracyclo [8.4.1.1 ^8.13 0 ^2.7 ] hexadeca-2,6-diene, which is obtained by a known method [Kuznetsov A.I., Vladimirova I.A., Basargin E.B. and other Heteroadamantanes and their derivatives. II. Synthesis of 3,6-diazagomoadamantan-9-one and its derivatives with substituents in nodal positions // CGS. - 1990. - No. 5. - S.675-680] was stirred in an aqueous solution in the presence of hydrochloric acid and sodium nitrite for 0.5 h at room temperature. The reaction mass was neutralized with an aqueous solution of potash, water was evaporated in vacuo, the solid residue was extracted with heptane. After recrystallization from heptane, 1,8-dimethyl-3,6-diazadigomoadamantan-9,10-dione was obtained. The yield of the compound was 78%. The synthesis is carried out according to the following scheme:

Example 1

1,8-Dimethyl-3,6-diazagomoadamantan-9,10-dione

A solution of 0.1 g of 1,8-dimethyl-3,6,10,13-tetrazatetetracyclo [8.4.1.1 ^8.13 -0 ^2.7 ] hexadeca-2,6-diene in 2 ml of water in the presence of 0.5 ml of hydrochloric acid and 0.03 g of sodium nitrite were stirred for 0.5 h at room temperature. The reaction mass was neutralized with an aqueous solution of potash, water was evaporated in vacuo, the solid residue was extracted with heptane. After percrystallization from heptane, 0.07 g (78%) of the compound was obtained. _Mp 108-109 ° C. IR spectrum υ, cm ^-1 : 1750, 1720 (С = O). ¹ H-NMR spectrum δ, ppm: 2.90 d (4H, NCH ₂ CH ₂ N); 3.22 m (8H, NCH ₂ C), 1.02 s, (3H, CH ₃ ), ¹³ C-NMR spectrum, δ, ppm: 208 (C-9.10), 62.5 ( C-4.5), 57.8 (C-2.7.11, 12), 53.5 (C-1.8), 20 (CH ₃ ). Elemental analysis, calculated,%: C 64.86, H 8.10, N 12.60, O 14.40, found,%: C 64.80, H 8.12, N 12.63, O 14.41 .

The individuality of the compounds was confirmed by a combination of IR, ¹ H-NMR- ¹³ C-NMR spectroscopy, as well as elemental analysis.

Thus, this method allows to obtain 1,8-dimethyl-3,6-diazagomoadamantan-9,10-dione, which can be used as an antiviral drug.

Claims (1)

The method of obtaining 1,8-dimethyl-3,6-diazadigomoadamantane-9,10-dione, which consists in the interaction of 1,8-dimethyl-3,6,10,13-tetrazate tetracyclo [8.4.1.1 ^8.13 0 ^2,7 ] hexadeca-2,6-diene with water in the presence of hydrochloric acid and sodium nitrite at room temperature.