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1.
I. E. Yakunina A. N. Shchukin M. V. Kopyshev I. V. Shakhkel’dyan A. N. Shumskii A. A. Yakovenko K. A. Lysenko Yu. M. Atroshchenko 《Russian Journal of Organic Chemistry》2011,47(6):877-880
Reduction of 6-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes gives either saturated 1,5-diamino-3-azabicyclo[3.3.1]nonane
or unsaturated 1,5-diamino-3-azabicyclo[3.3.1]non-6-enes, depending on the conditions and nature of substituent in the substrate. 相似文献
2.
I. V. Shakhkeldyan Yu. M. Atroshchenko N. K. Melekhina I. E. Yakunina K. I. Kobrakov A. N. Shumsky 《Chemistry of Heterocyclic Compounds》2008,44(6):690-699
The electrophilic addition of bromine to 3-substituted 1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene in carbon tetrachloride is
accompanied by intramolecular 3,7-cyclization with the formation of 6-bromo-3-R-1,5-dinitro-3-azonia-tricyclo[3.3.103,7]nonane tribromides. In the bromination of 1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes containing substituents at the double
bond, molecular complexes of halogen with the substrate were obtained.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 862–873, June, 2008. 相似文献
3.
Shakhkel' I.V. Nikiforova E.G. Grudtsyn Yu.D. Atroshchenko Yu.M. Borbulevich O.Ya. Efremov Yu.A. Gitis S.S. Moiseev D.N. Alifanova E.N. Chudakov P.V. Kovalevskii A.Yu. 《Russian Journal of Organic Chemistry》2001,37(4):583-591
A series of 1.5-dinitro-3-azabicyclo[3.3.1]non-6-enes was prepared by reduction of 1-R-2,4- and 1-R-3,5-dinitrobenzenes with potassium borohydride followed by Mannich reaction with formaldehyde and amino acids. The molecular structure of (6-bromo-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic acid was studied by X-ray diffraction analysis. The mechanism of decomposition under electron impact was determined for (7-methoxy-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-3-yl)acetic acid. 相似文献
4.
Kopyshev M. V. Shakhkeldyan I. V. Kozlova L. M. Litvin E. F. Sharf V. Z. Troitskii N. A. Atroshchenko Yu. M. Alifanova E. N. Nikishina M. B. Vorontsov I. N. Gurylev D. V. 《Russian Journal of Organic Chemistry》2004,40(2):255-260
During catalytic reduction with hydrogen on nickel of a series of 3-substituted 1,5-dinitro-3-azabicyclo-[3.3.1]non-6-enes alongside nitro groups reduction occurred also hydrogenation of the double bond. New diamines of the 3-azabicyclo[3.3.1]nonane series were synthesized, and their structure was established by means of IR, 1H and 13C NMR spectroscopy and X-ray diffraction study. 相似文献
5.
Shahkel'dyan I. V. Melekhina E. K. Atroshchenko Yu. M. Efremov Yu. A. Alifanova E. N. Kopyshev M. V. Troitskii N. A. Subbotin V. A. Nikishina M. B. 《Russian Journal of Organic Chemistry》2003,39(4):589-595
A series of 7-carboxy-3-R-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes was synthesized by reduction of 3,5-dinitrobenzoic acid with sodium borohydride followed by Mannich reaction with formaldehyde and primary amines. The mechanism of decomposition under electron impact of the 3-azabicyclo[3.3.1]nonane was established. Enthalpies of formation of compounds synthesized were calculated by semiempirical PM3 method. 相似文献
6.
E. G. Nikiforova M. A. Korolev I. V. Shakhkel''dyan M. D. Dutov Yu. D. Grudtsyn Yu. M. Atroshchenko S. A. Shevelev V. A. Subbotin 《Russian Journal of Organic Chemistry》2001,37(5):734-738
A number of 7-polyfluoroalkoxy-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes were synthesized by reduction of 3,5-dinitrophenyl polyfluoroalkyl ethers with sodium tetrahydridoborate, followed by the Mannich reaction with formaldehyde and primary amines. 相似文献
7.
Iurenkov M. V. Potapova T. V. Baranin S. V. Bubnov Yu. N. 《Russian Chemical Bulletin》2021,70(10):1987-1993
Russian Chemical Bulletin - An efficient synthesis of 7-substituted 3-azabicyclo[3.3.1]non-6-enes from available 3-borabicyclo[3.3.1]non-6-enes, the products of allylboron-acetylene condensation,... 相似文献
8.
Shakhkeldyan I. V. Melekhina N. K. Atroshenko Yu. M. Kopyshev M. V. Borbulevich O. Ya. Suponitskii K. Yu. Antipin M. Yu. Alifanova E. N. Nikisina M. B. Subbotin V. A. 《Russian Journal of Organic Chemistry》2004,40(2):247-254
N-Alkylation of 6(7)-R-1,5-dinitro-3-methyl-3-azabicyclo[3.3.1]non-6-enes with methyl iodide afforded a series of quaternary ammonium salts whose yield depended on the solvent polarity and character of substituents located in positions 6 or 7 of substrate. The presence of electron-withdrawing groups reduced the yield of the target products compared to unsubstituted compound, whereas the electron-donor substituents increased the yield. As shown by the X-ray diffractionstudy the congormation of the substances was not changed in the course of quaternization. The DTA-TG analysis revealed that in the first stage of thermolysis the 6(7)-R-3,3-dimethyl-1,5-dinitro-3-azoniabicyclo[3.3.1]non-6-ene iodides suffer dealkylation. Two fragmentation paths of compounds synthesized under electron impact were observed: elimination either of methyl iodide or aziridinium cation. 相似文献
9.
Yu. M. Atroshchenko I. E. Shakhkel'dyan O. Ya. Borbulevich A. N. Shchukin M. Yu. Antipin V. N. Khrustalev 《Russian Journal of Organic Chemistry》2005,41(11):1683-1689
Anionic hydride adduct of 1-(2-hydroxyethoxy)-2,4-dinitrobenzene was brought into a double Mannich condensation with formaldehyde and methylamine to furnish a mixture of isomeric 3-azabicyclo[3.3.1]nonanes: 3-methyl-6-(2-hydroxyethoxy)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene and 3-methyl-6,6-ethylenedioxy-1,7-dinitro-3-azabicyclo[3.3.1]nonane. By means of NMR spectroscopy, X-ray difraction analysis, and quantum chemistry (PM3) we demonstrated that the spirocyclic isomer had chair-chair conformation with diequatorial orientation of substituents in positions 3 and 7. 相似文献
10.
Yarmukhamedov N. N. Baibulatova N. Z. Khakimova T. V. Spirikhin L. V. Dokichev V. A. Yunusov M. S. 《Russian Chemical Bulletin》2001,50(2):265-267
Reduction of the nitro groups in 3-(2-hydroxyethyl)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-ene was studied. The structures of the reaction products were confirmed using 1H and 13C NMR spectroscopy. 相似文献
11.
Shakhkel'dyan I. V. Leonova O. V. Atroshchenko Yu. M. Boikova O. I. Borbulevych O. Ya. Grintselev-Knyazev G. V. Yakunina I. E. Shchukin A. N. Alifanova E. N. Subbotin V. A. 《Russian Journal of Organic Chemistry》2003,39(11):1593-1602
By condensation of 2,4-bis(aci-nitro)-3-(2-phenyl-2-oxoethyl)cyclohex-5-en-1-one with formaldehyde and primary amines a series of N-substituted 9-(2-phenyl-2-oxoethyl)-1,5-dinitro-3-azabicyclo[3.3.1]non-7-en-6-ones was synthesized. With the use of X-ray analysis the cyclohexenone fragment in the 3-(2-bromoethyl)-1,5-dinitro-9-(2-phenyl-2-oxoethyl)-3-azabicyclo[3.3.1]non-7-en-6-ones was established to exist in sofa conformation, and the nitrogen-containing ring to have the chair conformation with equatorial orientation of substituents in 3 and 9 positions. The regio- and stereoselectivity of the reaction under study was interpreted relying on the quantum-chemical calculations by AM1 and PM3 procedures. 相似文献
12.
O. V. Leonova I. V. Shakhkel''dyan Yu. D. Grudtsyn Yu. M. Atroshchenko E. N. Alifanova S. S. Gitis P. V. Chudakov E. G. Nikiforova N. N. Alekhina A. Ya. Kaminskii 《Russian Journal of Organic Chemistry》2001,37(3):395-400
A number of 9-acetonyl-1,5-dinitro-3-azabicyclo[3.3.1]non-6-en-8-one derivatives were synthesized by Mannich condensation of 3-acetonyl-2,4-bis(aci-nitro)cyclohex-5-en-1-one disodium salt with formaldehyde and primary amines. 相似文献
13.
I. E. Yakunina Yu. M. Atroshchenko I. V. Shahkheldyan K. I. Kobrakov N. A. Troizkiy O. I. Boikova 《Chemistry of Heterocyclic Compounds》2007,43(9):1174-1180
Aminomethylation has been accomplished of the anionic Yanovskii adduct of 2,4-dinitronaphthol and 3,4-dimethylenedioxyacetophenone.
The structure of the 3-substituted 9-[2-(3,4-methylenedioxyphenyl)-2-oxoethyl]-1,5-dinitro-7,8-benzo-3-azabicylo[3.3.1]non-7-en-6-one
was determined by two-dimensional homo-and heteronuclear correlation spectroscopy.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, 1382–1389, September 2007. 相似文献
14.
M.E. Gurskii S.V. Baranin A.S. Shashkov A.I. Lutsenko B.M. Mikhailov 《Journal of organometallic chemistry》1983,246(2):129-139
The ate complexes of 7-substituted 3-alkyl-3-borabicyclo[3.3.1]nonanes and of 3-alkyl-3-borabicyclo[3.3.1]non-6-enes react with acetyl chloride under mild conditions by an intermolecular β-hydride transfer mechanism to form 5-substituted 3-methylenecyclohex-1-ylmethyl(dialkyl)boranes. The latter compounds were converted, by oxidation with alkaline hydrogen peroxide, to 3-substituted 1-methylene-5-hydroxymethylcyclohexanes. The reaction of cycloalkylmethyl(dialkyl)boranes with aromatic aldehydes was applied to the synthesis of 1,3-di- and 1,3,5-tri-methylene derivatives of the cyclohexane series. 相似文献
15.
S. E. Sosonyuk M. N. Bulanov I. F. Leshcheva N. V. Zyk 《Russian Chemical Bulletin》2002,51(7):1254-1261
Addition of bromine and potassium dihaloiodates(i) to 2-alkyl-2-azabicyclo[2.2.1]hept-5-enes and 2-alkyl-2-azabicyclo[2.2.2]oct-5-enes affords quaternary ammonium salts containing the aziridine ring and the polyhalide anion. The possibility of using these salts for the synthesis of 6-substituted 2-alkyl-2-azabicyclo[2.2.1]heptanes has been shown. 相似文献
16.
A facile and operationally simple route to diastereomerically pure, natural-like 3-azabicyclo[3.3.1]non-6-enes via microwave-assisted, BF3·OEt2-promoted aza-Prins reaction has been developed. Complexity-generating transformations based on these products involving reactive functionalities introduced during the aza-Prins step have been developed. 相似文献
17.
Condensation of 3-substituted 3-azabicyclo[3.3.1]nonan-9-ones with hydroxylamine and hydrazine hydrate gave the corresponding oximes, hydrazones, and azines. Reductive amination of the title compounds in the presence of sodium triacetoxyhydridoborate led to the formation of 3-substituted 3-azabicyclo[3.3.1]nonan-9-amines which were converted into the corresponding dihydrochlorides by treatment with dry hydrogen chloride. Treatment of 3-tert-butoxycarbonyl derivatives with HCl under analogous conditions was accompanied by elimination of the tert-butoxycarbonyl group to produce 3-azabicyclo[3.3.1]nonan-9-amine dihydrochlorides. 相似文献
18.
A. V. Puchnin M. A. Bastrakov A. M. Starosotnikov S. V. Popkov S. A. Shevelev 《Russian Chemical Bulletin》2012,61(3):596-599
The previously unknown 3-R-1,5-dinitro-3-azabicyclo[3.3.1]nonanes fused to the pyrazole or thiazole rings were synthesized by the reductive cyclization of m-dinitroindazoles and benzothiazoles. The method is based on the reduction of carbon-carbon bonds in the benzene ring, which are activated by the meta-nitro groups, with NaBH4 followed by the Mannich reaction with formaldehyde and primary amines. 相似文献
19.
Yakunina I. E. Shakhkeldyan I. V. Atroshenko Yu. M. Borbulevich O. Ya. Nesterov V. V. Kopyshev M. B. Troitskii N. A. Efremov Yu. A. Alifanova E. N. Subbotin V. A. 《Russian Journal of Organic Chemistry》2004,40(2):239-246
A number of 3-R-9-(2-oxopropyl)-1,5-dinitro-7,8-benzo-3-azsbicyclo[3.3.1]non-7-en-6-ones was synthesized by Mannich reaction involving Yanovsky adduct of 2,4-dinitronaphthol. It was established by molecular spectroscopy and X-ray diffraction analysis that the piperidine ring in these compounds was in the chairconformation with a diequatorial position of the substituent attached to the heteroatom and 2-oxo-propyl group, and the cyclohexenone fragment was in sofaform. By an example of 3-methyl-9-(2-oxopropyl)-1,5-dinitro-7,8-benzo-3-azsbicyclo[3.3.1]non-7-en-6-one the dissociative ionization of bicyclononanes under the electron impact was investigated. 相似文献
20.
G. G. Trigo P. Ballesteros M. Espada E. Santos E. Glvez C. Avendao M. Martínez 《Journal of heterocyclic chemistry》1980,17(7):1417-1424
The mass spectra of some N-substituted nortropane and granataninespirohydantoins are compared with those of N-substituted 3-azabicyclo[3.2.1]octane-8-spiro-, 3-azabicyclo[3.3.1]nonane-9-spiro-, 8-azabicyclo-[4.3.1]decane-10-spiro- and 3,7-diazabicyclo[3.3.1]nonane-9-spiro-5′-hydantoins. Mass spectra data of monothio- and dithio-tropanespirohydantoins are also included. Mass fragmentation and structure relationships of these molecules have been established. 相似文献