I. A. Vladimirova

Heteroadamantanes and their derivatives

Abstract9-Amino-3,6-diazahomoadamantanes were prepared from 3,6-diazahomo-adamantan-9-ones through oximes and converted into 9-acetylamino-3,6-diaza-homoadamantanes with acetic anhydride. It was shown that oximes with one substituent in the nodal position are formed as one geometric isomer with the E-position of the hydroxyl group relative to the substituent.

Heteroadamantanes and their derivatives 11. Synthesis of 3,6-diazahomoadamantan-9-one and its derivatives with substituents in the angular positions

The condensation of ketones with tetramethylenediethylenediamine led to the isolation of 3,6-diazahomoadamantan-9-one and its derivatives with substituents in the angular positions; their structure was confirmed by the data of the IR, PMR, and mass spectra.

Heteroadamantanes and their derivatives. 17. Wolff—Kishner reduction of 3,6-diazahomoadamantan-9-ones

Wolff—Kishner reduction of the keto group of 3,6-diazahomoadamantan-9-ones to a methylene group was investigated. It was shown that diazahomoadamantanones yield hydrazones in the reaction with hydrazine hydrate, and they are converted into 3,6-diazahomoadamantane derivatives with one or two substituents in nodal positions when heated with a base. Unsubstituted 3,6-diazahomoadamantane is not formed in these conditions, since 3,6-diazahomoadamantan-9-one hydrazone is convened into azine when heated above 70‡C. Other hydrazones are also converted into azines when heated, but at a higher temperature —above 150‡C.

Heteroadamantanes and their derivatives. 14. Synthesis of 3,6-diazahomoadamantan-9-ols and their acetates

The reduction of 3,6-diazahomoadamantan-9-ones with metal hydrides gave 3,6-diazahomoadamantan-9-ols, which were convened to acetates by the action of acetic anhydride. The effect of the substituents in the nodal positions on the rates of reduction and acylation is demonstrated.

Heteroadamantanes and their derivatives. 23. Reduction of nitroaryl derivatives of 3,6-diazahomoadamantane

It has been found that nitroaryl derivatives of diazahomoadamantane can be reduced selectively by hydrazine. New data are presented on the noncatalytic reduction of p-nitrophenyldiazahomoadamantane by hydrazine hydrate.