共查询到20条相似文献,搜索用时 31 毫秒
1.
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
2.
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
3.
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
4.
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
5.
Facile synthesis of derivatives of 2,4-diphenyl-3-azabicyclo[3.3.1]nonane and 7,9-diphenyl-8-azabicyclo[4.3.1]decane The facile synthesis of hydantoins, cyanhydrins and aminonitriles derived from 2,4-diphenyl-3-azabicyclo[3.3.1]nonanone and 7,9-diphenyl-8-azabicyclo[4.3.1]decanone is described. Configurations at C(9) or C(10) of the new compounds wth pharmaceutical and synthetical utility is deduced from their spectral properties. 相似文献
6.
R. Jeyaraman Cooksley Baldwin Jawaharsingh S. Avila K. Ganapathy Ernest L. Eliel Muthiah Manoharan Susan Morris-Natschke W. R. Kenan 《Journal of heterocyclic chemistry》1982,19(3):449-458
The 13C nmr spectra of 4 cis-2,4-diphenyl-3-azabicyclo[3.3.1]nonanes, 11 cis-2,4-diaryl-3-azabicyclo[3.3.1]-nonan-9-ones, 26 cis-2,4-diaryl-3-azabicyclo[3.3.1]-nonan-9-ols or acetates thereof, 5 cis-2,4-diaryl-3-azabi-cyclo[4.3.1]decan-10-ones or -10-ols and 5 cis-2,4-diphenyl-3-aza-7-thiabicyclo[3.3.1]nonan-9-ones, -9-ols or 9-yl acetates have been recorded. Except for the 7-thia compounds, which appear to exist mainly in the configuration and conformation with the nitrogen-containing ring in the boat form, these compounds seem to exist overwhelmingly in chair-chair conformations. The configuration of the 9-ols and their acetates (syn or anti to the nitrogen-containing ring) has been deduced from the spectra. In a number of cases, the structures assigned differ from those earlier postulated. Broadening of one set of aryl signals (probably those due to the ortho carbons) in the case of N-methyl (but not N-H) compounds without ortho substituents is ascribed to restricted phenyl rotation. 相似文献
7.
V. K. Yu K. D. Praliev E. E. Fomicheva R. D. Mukhasheva S. G. Klepikova 《Chemistry of Heterocyclic Compounds》2006,42(4):512-519
New 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-ones were synthesized by the double Mannich cyclization of tetrahydrothiopyran-4-one
with suitable alkoxyalkylamines and paraformaldehyde in acetous methanol. Wolff-Kishner decarbonylation of these bicyclic
ketones gave 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonanes. The reduction of 7-alkoxyalkyl-3-thia-7-azabicyclo[3.3.1]nonan-9-ones
by alkali metal hydride complexes leads to a mixture of two stereoisomeric secondary alcohols, which are epimers at C(9). Active analgesic, antiarrhythmic, and antibacterial compounds were found among these products.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 585–592, April, 2006. 相似文献
8.
A. I. Moskalenko A. Yu. Chashchin V. I. Boev 《Russian Journal of Organic Chemistry》2011,47(7):1003-1010
Catalytic hydrogenation of 3-benzyl- and 3-tert-butoxycarbonyl-3-azabicyclo[3.3.1]nonan-9-one oximes over Raney nickel gave the corresponding 3-substituted 3-azabicyclo[3.3.1]nonan-9-amines
which were converted into amides via reactions with acetyl and chloroacetyl chlorides and maleic and succinic anhydrides,
into Schiff bases by condensation with benzaldehyde and 4-chlorobenzaldehyde, and into isothiocyanates by treatment with thiophosgene
in the presence of K2CO3. 3-Benzyl- and 3-tert-butoxycarbonyl-3-azabicyclo-[3.3.1]nonan-9-yl isothiocyanates readily reacted with methanol, aniline, and sodium azide to
produce methyl thiocarbamate, thiourea, and dihydrotetrazole-5-thione derivatives having a 3-azabicyclo[3.3.1]nonane fragment. 相似文献
9.
Yu. M. Atroshchenko N. K. Melekhina I. V. Shakhkel’dyan I. E. Yakunina A. N. Shchukin E. V. Shuvalova V. A. Subbotin 《Russian Journal of Organic Chemistry》2006,42(8):1220-1224
The electrophilic chlorine addition to 3-substituted 1,5-dinitro-3-azabicyclo[3.3.1]-non-6-enes in the tetrachloromethane is accompanied at an intramolecular 3,7-cyclization giving 6-chloro-3-R-1,5-dinitro-3-azoniatricyclo[3.3.1.03,7]nonane chlorides. The reaction of the tricyclic quaternary ammonium salts with sodium methoxide leads to the formation of dealkylated and dehydrohalogenated products, 3-substituted 8-chloro-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes, bicyclic products with a halogen atom in an allyl position with respect to the double bond. 相似文献
10.
F Diaba A Martínez-Laporta J Bonjoch A Pereira JM Muñoz-Molina PJ Pérez TR Belderrain 《Chemical communications (Cambridge, England)》2012,48(70):8799-8801
A novel synthetic entry to 2-azabicyclo[3.3.1]nonanes based on a copper(i)-catalyzed intramolecular coupling of amino-tethered trichloroacetamides and unsaturated nitriles, esters and alkenes, as well as enol acetates, is described. A study of the reaction conditions and the scope of the process is reported. 相似文献
11.
3-Methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-α(β)-ols have been synthesized and studied by ir, 1H and 13C nmr spectroscopy. In deuteriochloroform and perdeuteriobenzene solutions, these compounds adopt a flattened chair-chair conformation in which the cyclohexane ring is more flattened. From the 1H and 13C nmr data, several stereoelectronic effects have been deduced. The complete and unambiguous assignment of all protons of the 3-azabicyclo[3.3.1]nonane system, not described up to date, has been carried out. 相似文献
12.
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
13.
Craig M. Williams 《Tetrahedron》2005,61(15):3771-3779
Specific 3-azabicyclo[3.3.1]nonane derivatives undergo skeletal cleavage when subjected to light or Lewis acidic conditions affording novel heterotricycles, which is in stark contrast to 3-oxabicyclo[3.3.1]nonanes. 相似文献
14.
Dirhodium(II)‐Catalyzed Annulation of Enoldiazoacetamides with α‐Diazoketones: An Efficient and Highly Selective Approach to Fused and Bridged Ring Systems 下载免费PDF全文
Dr. Qing‐Qing Cheng Julietta Yedoyan Dr. Hadi Arman Prof. Dr. Michael P. Doyle 《Angewandte Chemie (International ed. in English)》2016,55(18):5573-5576
A dirhodium(II)‐catalyzed annulation reaction between two structurally different diazocarbonyl compounds furnishes the donor–acceptor cyclopropane‐fused benzoxa[3.2.1]octane scaffold with excellent chemo‐, regio‐, and diastereoselectivity under exceptionally mild conditions. The composite transformation occurs by [3+2]‐cycloaddition between donor–acceptor cyclopropenes generated from enoldiazoacetamides and carbonyl ylides formed from intramolecular carbene–carbonyl cyclization in one pot with one catalyst. The annulation products can be readily transformed into benzoxa[3.3.1]nonane and hexahydronaphthofuran derivatives with exact stereocontrol. This method allows the efficient construction of three fused and bridged ring systems, all of which are important skeletons of numerous biologically active natural products. 相似文献
15.
《Tetrahedron: Asymmetry》1999,10(12):2399-2410
The first synthesis of enantiomerically pure 2-azabicyclo[3.3.1]nonanes by an intramolecular radical reaction of the trichloroacetamido group bearing an (S)-N-1-phenylethyl substituent with the silyl enol ether moiety in compounds 7 is described. The procedure allows the two enantiomers of the 2-azabicyclo[3.3.1]nonane-3,6-dione, 3 and ent-3, to be prepared separately. β-Lactam 8 and normorphan 9 are also formed from 7 through an initial radical translocation process in the cyclization step. 相似文献
16.
Synthesis of Spyrohydantoines Derivatives of 2,4-Diphenyl-3-azabicyclo[3.3.1]nonane and 7,9-Diphenyl-8-azabicyclo[4.3.1]decane via Bucherer Reaction in N,N-Dimethylformamide: Influence of the Temperature and Stereochemical Path The unreactives ketones related to 2,4-diphenyl-3-azabicyclo [3.3.1]nonan-9-one to the Bucherer reaction in usuals conditions show excellent reactivity in DMF. as unique solvant. The stereochemical paths of these reactions and the synthetic utility of the temperature modification are described. 相似文献
17.
Condensation of N-substituted 3-azabicyclo[3.3.1]nonan-9-ones with difunctional N,N-, N,S-, and N,O-centered nucleophiles (o-phenylenediamine, 1,2-diphenylethane-1,2-diamine, 2-aminobenzenethiol, cysteine, 2-aminophenol, serine) gave the corresponding spiro heterocyclic compounds fused at the C9 atom. Treatment of N-tert-butoxycarbonyl-substituted spiro compounds with anhydrous hydrogen chloride resulted in elimination of the tert-butoxycarbonyl group with formation of spiro[3-azabicyclo[3.3.1]nonane-9,2′-azole] hydrochlorides. 相似文献
18.
Dr. Guangde Jiang Dr. Chunshuai Huang Wesley Harrison Hongxiang Li Megan Zhou Prof. Huimin Zhao 《Angewandte Chemie (International ed. in English)》2023,62(22):e202302125
Herein we report that ene reductases (EREDs) can facilitate an unprecedented intramolecular β-C−H functionalization reaction for the synthesis of bridged bicyclic nitrogen heterocycles containing the 6-azabicyclo[3.2.1]octane scaffold. To streamline the synthesis of these privileged motifs, we developed a gram-scale one-pot chemoenzymatic cascade by combining iridium photocatalysis with EREDs, using readily available N-phenylglycines and cyclohexenones that can be obtained from biomass. Further derivatization using enzymatic or chemical methods can convert 6-azabicyclo[3.2.1]octan-3-one into 6-azabicyclo[3.2.1]octan-3α-ols, which can be potentially utilized for the synthesis of azaprophen and its analogues for drug discovery. Mechanistic studies revealed the reaction requires oxygen, presumably to produce oxidized flavin, which can selectively dehydrogenate the 3-substituted cyclohexanone derivatives to form the α,β-unsaturated ketone, which subsequently undergoes spontaneous intramolecular aza-Michael addition under basic conditions. 相似文献
19.
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
20.
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