One of the interesting classes of heterocyclic compounds are azabicyclo[3.3.1]nonanes. First of all this is because the azabicyclo skeleton is found as a structural unit in the composition of natural biologically active compounds possessing neurotropic, antiarrhythmic, and anticancer properties [1][2][3][4][5]. Many compounds which predominantly affect the κ-opioid receptors have found practical use after clinical testing [6][7][8][9]. Moreover, bicyclononanes and their heteroanalogs are suitable models for the study of the influence of intramolecular interactions on the conformational behavior of organic compounds.Nitro derivatives of aromatic hydrocarbons are unique sources for the synthesis of heterocyclic compounds [10]. On addition of nucleophilic agents to 1,3-dinitroarenes stable σ-complexes are formed which possess high reactivity in electrophilic reactions, and take part as CH-acid components in the Mannich reaction with the formation of 3-azabicyclo[3.3.1]nonanes. We have previously studied the aminomethylation of the anionic Yanovskii adduct of 2,4-dinitronaphthol and acetone [11]. In a continuation of this work we have investigated the possibility of using 3,4-methylenedioxyacetophenone as the source of the carbanion in this reaction.The method of synthesis includes several stages, the first of which consists of the preparation of the disodium salt of the Yanovskii σ-adduct 1 by the reaction of sodium ethoxide on the solution of 2,4-dinitronaphthol and 3,4-methylenedioxyacetophenone in ethanol. The anionic intermediate was precipitated from the reaction mixture with ether. The orange-red crystals in the precipitate were washed first with absolute ethanol and then with absolute ether. The reaction occurred in almost quantitative yield. In the next stage the __________________________________________________________________________________________ 1 L. N. Tolstoi

There are two mol­ecules, A and B, in the asymmetric unit of the title compound, C34H34N6O12. In both mol­ecules, the eight‐membered ring has a conformation which is close to a boat—boat conformation and the cyclo­hexene ring is characterized by a sofa conformation. The nitro groups in each mol­ecule are situated in equatorial positions. Both nitro groups of mol­ecule A are considerably rotated with respect to the flattened fragment of the cyclo­hexene ring. The same is true for one of the nitro groups of mol­ecule B, whereas the other such group in mol­ecule B is almost coplanar with the corresponding fragment.

Synthesis of N-Substituted 9-[2-(3,4-Methylenedioxyphenyl)-2-oxoethyl]-1,5-dinitro-7,8-benzo-3-azabicyclo[3.3.1]non-7-en-6-ones.-The Yanovskii σ-adduct (III), existing as disodium salt, underwents a straight aminomethylation reaction to the bicyclic products (VI). The compliance with a pH value between 5 and 6 (adjusted with 20% orthophosphoric acid) is described as determining factor because of the instability of the intermediate (III) and because of a concurrent protonation reaction. -(YAKUNINA, I. E.; ATROSHCHENKO, Y. M.; SHAHKHELDYAN, I. V.; KOBRAKOV, K. I.; TROIZKIY, N. A.; BOIKOVA, O. I.; Chem. Heterocycl. Compd. (N. Y.) 43 (2007) 9, 1174-1180; Tolstoi Tula State Pedagog. Univ., Tula 300026, Russia; Eng.) -H. Haber 19-168