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1.
Victor V. Dotsenko Sergey G. Krivokolysko Victor P. Litvinov 《Monatshefte für Chemie / Chemical Monthly》2007,56(12):489-494
The reaction of N-methylmorpholinium 5-alkoxy-carbonyl-4-aryl-3-cyano-2-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with primary amines and
formaldehyde under mild conditions afforded 7-substituted alkyl 9-aryl-5-cyano-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1-carboxylates
in fair to good yields (52–74%). 相似文献
2.
Victor V. Dotsenko Sergey G. Krivokolysko Victor P. Litvinov 《Monatshefte für Chemie / Chemical Monthly》2007,138(5):489-494
Summary. The reaction of N-methylmorpholinium 5-alkoxy-carbonyl-4-aryl-3-cyano-2-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with primary amines and
formaldehyde under mild conditions afforded 7-substituted alkyl 9-aryl-5-cyano-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1-carboxylates
in fair to good yields (52–74%).
Third author was Deceased on February 26, 2007 相似文献
3.
M. J. Fernandez M. S. Toledano E. Glvez E. Matesanz M. Martínez-Ripoll 《Journal of heterocyclic chemistry》1992,29(4):723-740
A series of 3,7-dimethyl-9-amino-3,7-diazabicyclo[3.3.1]nonane-9-carbonitrile and 3,7-dimethyl-9-amino-3,7-diazabicyclo[3.3.1]nonane-9-carboxamide N-substituted have been synthesized and studied by 1 H and 13C nmr spectroscopy and the crystal structure of 3,7-dimethyl-9-benzylamino-3,7-diazabicyclo[3.3.1]nonane-9-carboxamide dihydrochloride ( IVb· 2HCl) has been determined by X-ray diffraction. The compounds studied display in deuteriochloroform, dimethyl sulfoxide-d6 and methanol-d4 the same preferred flattened chair-chair conformation with the methyl groups in equatorial position. The carboxamido group lies in a plane nearly perpendicular to the bispidine skeleton. The conformation and protonation sites of IVb· 2HCl in the crystal state and in deuterium oxide solution are discussed. 相似文献
4.
Anastasiya N. Khrustaleva Konstantin A. Frolov Victor V. Dotsenko Nicolai A. Aksenov Inna V. Aksenova Sergey G. Krivokolysko 《Tetrahedron letters》2017,58(50):4663-4666
The aminomethylation of 4,4-dialkyl-2,6-dioxopiperidine-3,5-dicarbonitriles (Guareschi imides) was studied for the first time. When the Guareschi imides were treated with primary aliphatic amines and an excess of formaldehyde, 2,4-dioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitriles were obtained in varying yields (15–67%). The structure of 9,9-dimethyl-7-(2-methylpropyl)-2,4-dioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitrile was studied by X-ray diffraction analysis. 相似文献
5.
1-Carbethoxy-2,4,6,8-tetraaryl-3,7-diazabicyclo[3.3.1] nonan-9-ones (1, 2) were synthesized and their 1H and 13C NMR data are reported. Chemical shifts and spectral assignments for 2,4,6,8-tetrakis(4-chlorophenyl)-3,7-diazabicyclo[3.3.1]nonan-9-one (3), 2,4,6,8-tetraphenyl-3-thia-7-azabicyclo[3.3.1]nonan-9-one (4) and 2,4,6,8-tetraaryl-3,7-diazabicyclo[3.3.1]nonanes (5-7) are also included. 相似文献
6.
G. L. Arutyunyan K. A. Gevorkyan A. D. Arutyunyan R. V. Paronikyan G. M. Stepanyan G. A. Panosyan 《Russian Journal of Organic Chemistry》2014,50(10):1480-1484
A number of new 1,3-diazaadamantane derivatives containing quinoline fragments on C2 have been synthesized by condensation of 1,5-dialkyl-3,7-diazabicyclo[3.3.1]nonan-9-one, 1,5-dimethyl-3,7-diazabicyclo-[3.3.1]nonan-9-ol, and 1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane with 2-oxo-1,2-dihydroquinoline-3-carbaldehyde, 2-chloro- and 2-iodoquinoline-3-carbaldehyde, and quinoline-2-carbaldehyde. 相似文献
7.
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
8.
Atanasov M Busche C Comba P El Hallak F Martin B Rajaraman G van Slageren J Wadepohl H 《Inorganic chemistry》2008,47(18):8112-8125
The reaction of the hexacyanometalates K3[M(1)(CN)6] (M(1) = Cr(III), Fe(III), Co(III)) with the bispidine complexes [M(2)(L(1))(X)](n+) and [M(2)(L(2))(X)](n+) (M(2) = Mn(II), Ni(II), Cu(II); L(1) = 3-methyl-9-oxo-2,4-di-(2-pyridyl)-7-(2-pyridylmethyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester; L(2) = 3-methyl-9-oxo-7-(2-pyridylmethyl)-2,4-di-(2-quinolyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarboxylic acid dimethyl ester; X = anion or solvent) in water-methanol mixtures affords trinuclear complexes with cis- or trans-arrangement of the bispidine-capped divalent metal centers around the hexacyanometalate. X-ray structural analyses of five members of this family of complexes (cis-Fe[CuL(2)]2, trans-Fe[CuL(1)]2, cis-Co[CuL(2)]2, trans-Cr[MnL(1)]2, trans-Fe[MnL(1)]2) and the magnetic data of the entire series are reported. The magnetic data of the cyanide bridged, ferromagnetically coupled cis- and trans-Fe[ML]2 compounds (M = Ni(II), Cu(II)) with S = 3/2 (Cu(II)) and S = 5/2 (Ni(II)) ground states are analyzed with an extended Heisenberg Hamiltonian which accounts for anisotropy and zero-field splitting, and the data of the Cu(II) systems, for which structures are available, are thoroughly analyzed in terms of an orbital-dependent Heisenberg Hamiltonian, in which both spin-orbit coupling and low-symmetry ligand fields are taken into account. It is shown that the absence of single-molecule magnetic behavior in all spin clusters reported here is due to a large angular distortion of the [Fe(CN)6](3-) center and the concomitant quenching of orbital angular momentum of the Fe(III) ((2)T2g) ground state. 相似文献
9.
Altynay B. Kaldybayeva Valentina K. Yu Aigul E. Malmakova Tamara Li Assel Yu. Ten Tulegen M. Seilkhanov Kaldybay D. Praliyev Kenneth D. Berlin 《Molecules (Basel, Switzerland)》2022,27(21)
We report the syntheses and characterization of novel 3,7-bicycl[3.3.1]bispidines possessing an imidazolpropyl group attached to N-3, and at N-7 a Boc group, as well as a benzoylated-oximated group at C-9. These compounds were complexed with β-cyclodextrin [β-CD] and evaluated as seed protectors of selected wheat seedlings. Using strong acid, condensations of N-substituted piperidones with the appropriate imidazolpropyl groups at N-3 and N-7 led to bispidinones 6 and 7. These intermediates were reduced to the corresponding 3,7-diazabicyclo[3.3.1]nonane targets. The oxime at C-9 was benzoylated to yield 13. Heating these 3,7-diazabicyclo[3.3.1]nonanes in ethanol with β-CD generated the complexes required. We investigated the ability of such complexes as coatings on seedlings to protect and stimulate growth of three varieties of wheat, namely Kazakhstanskaya-10, Severyanka, and Miras. The complex of 3-[3-(1H-imidazol-1-yl)propyl]-7-(3-methoxypropyl)-3,7-diazabicyclo[3.3.1]nonane (2) promoted growth in the root systems of all three wheat varieties by more than 30% in Kazakhstanskaya-10, 30% in Severyanka and 8.5% in Miras. A complex of 3-Boc-7-[3-(1H-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonane (9) increased both shoot and root length in only the Severyanka variety. The complex of 3-(3-butoxypropyl)-7-[3-(1H-imidazol-1-yl)propyl]-3,7-diazabicyclo[3.3.1]nonane (11) stimulated both shoot growth (0.8%, 12.3%, 13.5%) and root growth (12.3%, 9.4%, 21.7%) in all three varieties of wheat, respectively. The nature of substituents on the bispidine affect the activity. Solid complexes (1:1) were generated as powders which melted above 240 °C (dec) and were characterized via elemental analyses as 1:1 complexes. 相似文献
10.
M. J. Fernandez J. M. Casares E. Galvez P. Gmez-Sal R. Torres P. Ruiz 《Journal of heterocyclic chemistry》1992,29(7):1797-1804
A series of methyl-2,6-diaryl-1-methyl-4-oxopiperidine-3,5-dicarboxylates Ia-c and 2,4-diaryl-3,7-dimethyl-1,5-dimethoxycarbonyl-9-bispidinones IIa-c have been synthesized and studied by ir, 1H and 13C nmr spectroscopy and the crystal structure of methyl 2,4-diphenyl-3,7-dimethyl-9-oxo-3,7-diazabicyclo[3,3.1]nonane-1,5-dicarboxylate (IIa) has been determined by X-ray diffraction. The enolic form of compound Ia (I'a) was also studied. 相似文献
11.
By the reaction of 1,5-dimethyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane with isatin and a number of its derivatives, spiro(1,3-diazaadamantane-2,3′-oxindoles)
have been synthesized. In the case of 5-bromoisatin, either 3-(3-hydroxyoxindolyl)-3,7-diazabicyclo[3.3.1]nonane or the corresponding
spirane is obtained, depending on the temperature. The interaction of these products with acetic anhydride has been studied.
For communication 24, see [1].
A. L. Mndzhoyan Institute of Fine Organic Chemistry, Academy of Sciences of the Republic of Armenia, Erevan 375014. Translated
from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1490–1493, November, 1997. 相似文献
12.
D. R. Latypova N. Z. Baibulatova R. A. Khisamutdinov Yu. I. Murinov V. A. Dokichev 《Russian Journal of Inorganic Chemistry》2011,56(6):981-985
Complexation of copper(II) chloride, copper(II) triflate, and palladium(II) chloride with optically active L,L-3,7-bis[2-(4-hydroxyphenyl)-1-(methoxycarbonyl)ethyl]-1,5-di(ethoxycarbonyl)-3,7-diazabicyclo[3.3.1]nonan-9-one was studied. 相似文献
13.
A. V. Eremeev R. Nurdinov F. D. Polyak R. M. Zolotoyabko A. F. Mishnev M. F. Bundule Ya. Ya. Bleidelis 《Chemistry of Heterocyclic Compounds》1985,21(10):1086-1091
7-Thia-1,3-diazabicyclo[3.3.0]octane-2,4-diones and 7-thia-1,3-diazabicyclo[4.3.0]-nonane-2, 4-diones, as well as their thio analogs, were obtained by the reaction of (S)-1,3-thiazolidine-4-carboxylic and 1,4-tetrahydrothiazine-3-carboxylic acid esters with isocyanates and isothiocyanates. Intermediate reaction products, viz., heterocyclic derivatives of urea, were isolated. The three-dimensional structures of the 3-methyl-4-oxo-7-thia-1,3-diazabicyclo[3.3.0]octane-2-thione and 3-methyl-4-oxo-7-thia-1, 3-diazabicyclo[4.3.0]nonane-2-thione molecules were determined by x-ray diffraction analysis.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1327–1332, October, 1985. 相似文献
14.
N. V. Averina G. S. Borisova A. A. Borisenko N. S. Zefirov 《Russian Journal of Organic Chemistry》2001,37(7):957-963
UV irradiation of trans-trans-3,7-bis(arylmethylene)bicyclo[3.3.1]nonane-2,6-diones leads to their complete or partial transformation into the corresponding cis-cis isomers. Irradiation of trans-trans-3,7-bis(arylmethylene)bicyclo[3.3.1]nonane-2,6-diol in ether in the presence of CuCl results in intramolecular cyclization involving the exocyclic double bonds and one benzene ring to give exo-7endo-10-dihydroxy-2-phenyl-3,4-benzotetracyclo[4.3.3.18,11.01,6]tridecane. 相似文献
15.
A. I. Kuznetsov K. I. Romanova E. B. Basargin A. S. Moskovskii B. V. Unkovskii 《Chemistry of Heterocyclic Compounds》1990,26(4):461-465
Heating 1,5-dinitro-3,7-di(tert-butyl)-3,7-diazabicyclo[3.3.1]-nonane with concentrated hydrobromic acid gives 1,5-dinitro-3,7-diazabicyclo[3.3.1]nonane. Cyclization of the latter with various aldehydes and ketones gave a series of 2,2-disubstituted 5,7-dinitro-1,3-diazaadamantanes. The behavior of the synthesized compounds under electron impact has been studied.For Communication 8 see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 538–542, April, 1990. 相似文献
16.
L. I. Vlasova N. Z. Baibulatova V. A. Dokichev Yu. V. Tomilov 《Russian Chemical Bulletin》2012,61(11):2129-2132
One-pot reactions of dimethyl sulfonyldiacetate and N-methyl-2r,6c-di(methoxycarbonyl)-3t,5t-diphenyltetrahydro-1,4-thiazine 1,1-dioxide with formaldehyde and primary amines lead to derivatives of 9-thia-3,7-diazabicyclo[3.3.1]nonane 9,9-dioxide resulted from decarboxylation of the ester groups at the positions 1 and 5. The effects of the reaction conditions and structure of the starting reagents on the yields of 9-thia-3,7-diazabicyclo[3.3.1]nonane 9,9-dioxides were studied. 相似文献
17.
S. Z. Vatsadze V. S. Tyurin A. I. Zatsman M. A. Manaenkova V. S. Semashko D. P. Krut’ko N. V. Zyk A. V. Churakov L. G. Kuz’mina 《Russian Journal of Organic Chemistry》2006,42(8):1225-1231
The ring opening in the 1-benzyl-5,7-dimethyl-6-oxo-1-azonia-3-azaadamantane chloride under the treatment with excess aqueous alkali led to a stereoselective formation of anti-1,5-dimethyl-7-benzyl-3-formyl-3,7-diazabicyclo[3.3.1]nonan-9-ol whose structure was established by means of X-ray diffraction analysis and NMR spectroscopy. A reaction mechanism was suggested involving an intramolecular redox hydride transfer. 相似文献
18.
Ts. Ye. Aghajanian G. L. Arutyunian R. K. Shahkhatuni 《Chemistry of Heterocyclic Compounds》2003,39(6):767-770
Alternative methods for the synthesis of 2-spiro-substituted 6-hydroxy-5,7-dimethyl-1,3-diazaadamantanes have been developed. These are the reduction of the ketone group to hydroxyl in the corresponding 6-oxo-1,3-diazaadamantanes and the condensation of 9-hydroxy-1,5-dimethyl-3,7-diazabicyclo[3.3.1]nonane (obtained by different routes from 5,7-dimethyl-6-oxo-1,3-diazaadamantane) in reaction with cyclic ketones. 相似文献
19.
The activity of pharmacologically active compounds can be increased by presenting a drug in a defined conformation, which fits exactly into the binding pocket of its target. Herein, the piperazine scaffold was conformationally restricted by substituted C2- or C3-bridges across the 2- and 6-position. At first, a three-step, one-pot procedure was developed to obtain reproducibly piperazine-2,6-diones with various substituents at the N-atoms in high yields. Three strategies for bridging of piperazine-2,6-diones were pursued: 1. The bicyclic mixed ketals 8-benzyl-6-ethoxy-3-(4-methoxybenzyl)-6-(trimethylsilyloxy)-3,8-diazabicyclo[3.2.1]octane-2,4-diones were prepared by Dieckmann analogous cyclization of 2-(3,5-dioxopiperazin-2-yl)acetates. 2. Stepwise allylation, hydroboration and oxidation of piperazine-2,6-diones led to 3-(3,5-dioxopiperazin-2-yl)propionaldehydes. Whereas reaction of such an aldehyde with base provided the bicyclic alcohol 9-benzyl-6-hydroxy-3-(4-methoxybenzyl)-3,9-diazabicyclo[3.3.1]nonane-2,4-dione in only 10 % yield, the corresponding sulfinylimines reacted with base to give N-(2,4-dioxo-3,9-diazabicyclo[3.3.1]nonan-6-yl)-2-methylpropane-2-sulfinamides in >66 % yield. 3. Transformation of a piperazine-2,6-dione with 1,4-dibromobut-2-ene and 3-halo-2-halomethylprop-1-enes provided 3,8-diazabicyclo[3.2.1]octane-2,4-dione and 3,9-diazabicyclo[3.3.1]nonane-2,4-dione with a vinyl group at the C2- or a methylene group at the C3-bridge, respectively. Since bridging via sulfinylimines and the one-pot bridging with 3-bromo-2-bromomethylprop-1-ene gave promising yields, these strategies will be exploited for the synthesis of novel receptor ligands bearing various substituents in a defined orientation at the carbon bridge 相似文献
20.
I. V. Grishina D. V. Makeev V. B. Rybakov V. L. Lapteva V. A. Palyulin N. S. Zefirov 《Doklady Chemistry》2017,477(1):239-243
3,7-Ditosyl-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonane has been found to adopt a chair–chair conformation in the crystalline state in contrast to 3,7-ditosyl-1,5-diphenyl-3,7-diazabicyclo[3.3.1]nonan-9-one, which had been previously found to exist in a chair-boat conformation. 相似文献