114544-11-5Relevant academic research and scientific papers
HYDROAMINATION OF PYRYLIUM SALTS
Kriven'ko, A. P.,Fedotova, O. V.,Reshetov, P. V.,Kharchenko, V. G.
, p. 1361 - 1364 (1984)
Some pyrylium salts and condensed systems derived therefrom have been hydromethylaminated to saturated azaheterocycles and N-methylpyridinium salts.Attempts to hydroarylaminate pyrylium salts resulted in the formation of the corresponding hydrocarbons.
Hydroacridines. Part 31. Saturated amine oxides. Part 9. Study of a procedure for N-demethylation of saturated azaheterocyclic tertiary N-methylamines via their N-oxides
Potmischil, Francisc,Dobrinescu, Claudiu,Nicolescu, Alina,Deleanu, Calin
experimental part, p. 95 - 99 (2012/10/08)
The oxidative N-demethylation of the N-epimeric N-oxides of four stereoisomeric N-methyl-tetradecahydroacridines, with K2CrO 4, was performed with yields varying within 39-85%. The course and yield of the reaction is clearly influenced by the geometry of the tricyclic carbon framework of the parent amine, whereas the configuration of the N-methyl group (axial or equatorial) has no obvious influence upon yields.
Hydroacridines XVIII [1]. Synthesis and NMR spectroscopic investigation of (4aα,8aβ,9aα,10aβ)-tetradecahydroacridine and some of its derivatives
Potmischil, Francisc,Vierhapper, Friedrich W.,Kalchhauser, Hermann
, p. 515 - 522 (2007/10/03)
The reductive amination of (R*,R*)-2,2′-methylene-bis-cyclohexanone (1) with methylamine and potassium borohydride affords a mixture of (4aα,8aβ,9aα,10aβ)- and (4aα,8aα,9aβ,10aα)-tetradecahydro-10-methylacridine (2, 3) in a ratio of approximately 1.3:1 in 57% overall yield. By N-demethylation of 2, via the N-nitrosamine 4 the first synthesis of (4aα,8aβ,9aα,10aβ)-tetradecahydroacridine (5) could be performed. The relative configurations and conformations of compounds 2-5 as well as the barrier of conformational inversion of 5 (ΔG#300 = 55.5 ± 0.4 kJ · mol-1) were determined by NMR spectroscopy.
SATURATED NITROGEN-CONTAINING HETEROCYCLES. 13. PERHYDROACRIDINES. SYNTHESIS AND STEREOCHEMISTRY
Kriven'ko, A. P.,Nikolaeva, T. G.,Yudovich, L. M.,Komyagin, N. T.,Yanovskii, A. I.,et al.
, p. 1324 - 1329 (2007/10/02)
The configurations of the perhydroacridines formed in the catalytic hydroamination of threo-methylenedicyclohexanone and the product of its cyclization - 2-hydroxy-2,3-tetramethylenebicyclononan-9-one - were established by means of the 13C NMR spectra and alternative synthesis.It is shown that isomers with cis-anti-cis and cis-syn-cis configurations are formed as a result of the reactions.The results of X-ray diffraction analysis are presented for cis-syn-cis-N-(2-hydroxyethyl)perhydroacridine.
FORMATION OF NITROGEN HETEROCYCLES IN THE HYDROAMINATION OF 1,5-DIKETONES
Kharchenko, V. G.,Kriven'ko, A. P.,Fedotova, O. V.,Nikolaeva, T. G.
, p. 720 - 723 (2007/10/02)
It was established that the principal pathway in the catalytic hydro(alkyl,aryl)amination of 1,5-diketones is, depending on the structure of the diketone and the amine component, the stereospecific formation of substituted piperidines, octa- and decahydroquinolines, and perhydroacridines or pyridine and tetrahydro- and benzodihydroquinoline structures.
