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Journal articles on the topic '2-azabicyclo[3.3.1]octane'

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Published: 9 March 2023

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1

Kumaran, D., M. N. Ponnuswamy, G. Shanmugam, S. Ponnuswamy, R. Jeyaraman, K. Shivakumar, and H. K. Fun. "Molecular structures and conformations of three 3-azabicyclononanes." Acta Crystallographica Section B Structural Science 55, no. 5 (October 1, 1999): 793–98. http://dx.doi.org/10.1107/s0108768199005273.

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The structure, conformation, molecular geometry and the mode of packing of 7-tert-butyl-N-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonane (C25H33N; MTABN), N-acetyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonane (C22H25NO; AABN) and N-methyl-2,4-bis(2-methylphenyl)-3-azabicyclo[3.3.1]nonan-9-ol (C23H29NO; MHABN) are presented. The compounds MTABN and MHABN crystallize in monoclinic space groups, whereas AABN is orthorhombic. In each of the three structures, the bicyclic ring system adopts a chair–chair conformation and the phenyl rings are in equatorial orientation with respect to the piperidine ring. In AABN, apart from the van der Waals forces, weak intermolecular C—H...O type interactions are involved in the packing.

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2

Bonjoch, Josep, Nuria Casamitjana, Josefina Quirante, Antoni Torrens, Anna Paniello, and Joan Bosch. "Functionalized 2-azabicyclo[3.3.1] nonanes. vii." Tetrahedron 43, no. 2 (January 1987): 377–81. http://dx.doi.org/10.1016/s0040-4020(01)89966-x.

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3

Bonjoch, Josep, Faïza Diaba, and Ben Bradshaw. "Synthesis of 2-Azabicyclo[3.3.1]nonanes." Synthesis 2011, no. 07 (February 3, 2011): 993–1018. http://dx.doi.org/10.1055/s-0030-1258420.

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4

Parthiban, P., V. Ramkumar, Min Sung Kim, Se Mo Son, and Yeon Tae Jeong. "2,4-Bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (May 23, 2009): o1383. http://dx.doi.org/10.1107/s1600536809018686.

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In the title compound, C22H25NO3, the molecule has a pseudo-mirror plane. The structure is a positional isomer of 2,4-bis(4-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one [Cox, McCabe, Milne & Sim (1985).J. Chem. Soc. Chem. Commun.pp. 626–628]. The 3-azabicyclo[3.3.1]nonan-9-one moiety adopts a double chair conformation with equatorial orientations of both 2-methoxyphenyl substituents on either side of the secondary amino group. The benzene rings are oriented at an angle of 33.86 (4)° with respect to each other and the methoxy groups point towards the carbonyl group. The crystal structure is stabilized by intermolecular N—H...π interactions.

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5

Rao, T. N., Y. Prasanthi, Parvatamma Botsa, G. Kumara, and K. A. Rao. "A NEW METHOD DEVELOPMENT AND VALIDATION FOR RELATED SUBSTANCES OF GRANISETRON IN ACTIVE PHARMA INGREDIENT BY HPLC." INDIAN DRUGS 54, no. 07 (July 28, 2017): 52–59. http://dx.doi.org/10.53879/id.54.07.10746.

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A simple and inexpensive method was developed using high performance liquid chromatography with PDA detection for determination of granisetron hydrochloride and related impurities (2-methyl-N- [(1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]non-3-yl]-2H-indazole-3-carboxamide, 1-Methyl-N-[(1R,3r,5S)- 9-methyl-9-azabicyclo[3.3.1]non-3-yl]-1H-indazole-3-carboxamide hydrochloride, N-[(1R,3r,5S)-9- azabicyclo[3.3.1]non-3-yl]-1-methyl-1H-indazole-3-carboxamide and 1-methyl-1H-indazole-3-carboxylic acid. The chromatographic separations were achieved on (250×4.6 mm), 5.0 μm make: Waters, Symmetry Shield C8 column employing acetonitrile: 2% V/V H3PO4 in MilliQ water + 0.1% V/V hexylamine in water, 800:200 V/V (pH adjusted to 7.5 using triethylamine) mobile phase with isocratic programme. A flow rate of 1.5 mL/min was chosen. Four impurities were eluted within 20 minutes. The column temperature was maintained at 40°C and a detector wavelength of 300 nm was employed. The method was successfully validated by establishing system suitability, specificity, linearity, accuracy, limit of detection and limit of quantification.

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6

Eckermann, Ruben, Michael Breunig, and Tanja Gaich. "Formal total synthesis of (±)-strictamine – the [2,3]-Stevens rearrangement for construction of octahydro-2H-2,8-methanoquinolizines." Chemical Communications 52, no. 76 (2016): 11363–65. http://dx.doi.org/10.1039/c6cc06125g.

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7

Liu, Yan-Qing, He Liu, Bo-hua Zhong, Yu-Lin Deng, and Ke-liang Liu. "Synthesis and Crystal Structure of (9s)-N-methyl-3-azabicyclo[3.3.1] nonan-9-yl (cyclopentyl)(hydroxy)(2-thienyl)Acetate Hydrochloride." Journal of Chemical Research 2005, no. 7 (July 2005): 436–37. http://dx.doi.org/10.3184/030823405774309041.

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(9s)-N-methyl-3-azabicyclo[3.3.1]nonan-9-yl (cyclopentyl)(hydroxy)(2-thienyl)acetate hydrochloride, a more effective muscarinic receptor antagonist, was synthesised and its crystal structure elucidated by X-ray crystallography.

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8

Carman, Raymond M., and Roger P. C. Derbyshire. "Azacineole (1,3,3-Trimethyl-2-azabicyclo[2.2.2]octane)." Australian Journal of Chemistry 56, no. 4 (2003): 319. http://dx.doi.org/10.1071/ch02189.

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9

Grygorenko, Oleksandr, Maksym Kurkunov, Igor Levandovskiy, and Andriy Tymtsunik. "Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks." Synthesis 50, no. 10 (March 29, 2018): 1973–78. http://dx.doi.org/10.1055/s-0037-1609434.

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An approach to 2-azabicyclo[n.2.0]alkane derivatives (n = 1, 2), which relies on a tandem Strecker reaction–intramolecular nucleophilic cyclization (STRINC) sequence of the corresponding 2-(ω-chloroalkyl)cyclobutanones (in turn prepared by [2+2] cycloaddition of keteniminium salts and ethylene) is described. The utility of the method is demonstrated by multigram syntheses of bicyclic proline analogues, monoprotected diamines, as well as parent 2-azabicyclo[4.2.0]octane.

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10

Bonjoch, Josep, Faiza Diaba, and Ben Bradshaw. "ChemInform Abstract: Synthesis of 2-Azabicyclo[3.3.1]nonanes." ChemInform 42, no. 35 (August 4, 2011): no. http://dx.doi.org/10.1002/chin.201135229.

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11

Sridhar, B., K. Ravikumar, M. Mahesh, and V. V. Narayana Reddy. "(3Z)-2-Benzyl-3-benzylidene-6-phenyl-2-azabicyclo[2.2.2]octan-5-one." Acta Crystallographica Section E Structure Reports Online 63, no. 3 (February 28, 2007): o1500—o1501. http://dx.doi.org/10.1107/s1600536807009038.

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In the title compound, C27H25NO, all three rings in the azabicyclo[2.2.2]octane unit adopt a boat conformation. An intermolecular C—H...O interaction forms a characteristic R 2 2(14) motif dimer in the crystal packing.

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12

Chung, John Y. L., and Guo-Jie Ho. "AN IMPROVED PREPARATION OF 2-AZABICYCLO[2.2.2]OCTANE." Synthetic Communications 32, no. 13 (January 2002): 1985–95. http://dx.doi.org/10.1081/scc-120004848.

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13

Svoboda, Jiří, and Jaroslav Paleček. "New Method for Preparation of 1-Azabicyclo[2.2.2]octane-4-carbonitrile and 1-Azabicyclo[3.2.2]nonane-5-carbonitrile." Collection of Czechoslovak Chemical Communications 60, no. 9 (1995): 1536–40. http://dx.doi.org/10.1135/cccc19951536.

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The title compounds were prepared from pyridine-4-carboxamide. Its alkylation with 2-chloroethanol or 3-chloropropanol, followed by hydrogenation gave 1-substituted piperidine-4-carboxamides IIIa and IIIb, respectively, which on treatment with thionyl chloride were converted into the respective 1-substituted halogenoalkylpiperidine-4-carbonitriles IVa and IVb. On cyclization, compounds IVa and IVb afforded 1-azabicyclo[2.2.2]octane-4-carbonitrile and 1-azabicyclo[3.2.2]nonane-5-carbonitrile, respectively.

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14

Khaleel, Hind I., and Baidaa K. Al-Rubaye. "New Metal Complexes Derived from Heterocyclic Schiff-base Ligand; Preparation, Structural Investigation and Biological Activity." INTERNATIONAL JOURNAL OF DRUG DELIVERY TECHNOLOGY 12, no. 03 (June 30, 2022): 1341–46. http://dx.doi.org/10.25258/ijddt.12.3.68.

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The formation of a Schiff-base with N2O2 donor atoms derived from the hydrazine segment and its metal complexes are reported. The Schiff-base ligand; N’-((1R,2S,4R,5S,Z)-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)furan-2-carbohydrazide (HL) was prepared from the reaction of furan-2-carbohydrazide with (1R, 2R, 4R, 5S)-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-one (M1) in ethanol medium. The reaction of the title ligand with selected metal ions Cr(III), Mn(II), Ni(II), Cu(II), Zn(II) and Cd(II) gave complexes with the general formula [M(L)Cl2], (where: M = Cr(III), Mn(II), Ni(II), Cu(II), Zn(II) and Cd(II)). Spectroscopic analyses Fourier transform infrared (FT-IR), Nuclear Magnetic Resonance (NMR) Carbon-13 nuclear magnetic resonance (1H- and 13C-NMR), mass and electronic spectroscopy and atomic absorption) along with elemental microanalysis (C.H.N), chloride percentage, conductivity measurements, magnetic moments and melting point were used to establish the identity of ligand and complexes. The biological activity of the synthesized compounds towards bacterial strains (G+ and G-) was investigated.

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15

Williams, Steven Gareth, Mohan Bhadbhade, Roger Bishop, and Alison Thavary Ung. "Synthesis and Crystal Structure of Unexpected (1S,4R,5R,6S)-4-Cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonan-6-yl Acetate." Australian Journal of Chemistry 70, no. 12 (2017): 1269. http://dx.doi.org/10.1071/ch17270.

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The reaction of (–)-β-pinene with KCN under a mild bridged Ritter reaction gave (1S,5R,6S)-2,2,6-trimethyl-3-aza-bicyclo[3.3.1]non-3-en-6-yl acetate that subsequently reacted to provide an unexpected (1S,4R,5R,6S)-4-cyano-2,2,6-trimethyl-3-azabicyclo[3.3.1]nonane-6-yl acetate. The structure of the compound was determined by high-resolution mass spectrometry, and IR and NMR spectroscopy and confirmed by single crystal X-ray crystallography. The compound crystallises in the monoclinic P21 space group, with unit cell parameters a 8.6120 (17), b 7.4570 (15), c 11.189 (2) Å, and β 110.16 (3)°.

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16

BONJOCH, J., J. QUIRANTE, D. SOLE, J. CASTELLS, M. GALCERAN, and J. BOSCH. "ChemInform Abstract: Functionalized 2-Azabicyclo(3.3.1)nonanes. Part 14. 8-Aryl-2- azabicyclo(3.3.1)nonan-7-ones. Synthesis and Retro-Michael Ring Opening." ChemInform 22, no. 37 (August 22, 2010): no. http://dx.doi.org/10.1002/chin.199137260.

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17

Iwan, Dominika, Karolina Kamińska, Elżbieta Wojaczyńska, Mateusz Psurski, Joanna Wietrzyk, and Marek Daszkiewicz. "Biaryl Sulfonamides Based on the 2-Azabicycloalkane Skeleton—Synthesis and Antiproliferative Activity." Materials 13, no. 21 (November 6, 2020): 5010. http://dx.doi.org/10.3390/ma13215010.

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In a search for new, selective antitumor agents, we prepared a series of sulfonamides built on bicyclic scaffolds of 2-azabicyclo(2.2.1)heptane and 2-azabicyclo(3.2.1)octane. To this end, aza-Diels–Alder cycloadducts were converted into amines bearing 2-azanorbornane or a bridged azepane skeleton; their treatment with sulfonyl chlorides containing biaryl moieties led to the title compounds. The study of antiproliferative activity of the new agents showed that some of them inhibited the growth of chosen cell lines with the IC50 values comparable with cisplatin, and some derivatives were found considerably less toxic for nonmalignant cells.

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18

Parthiban, P., V. Ramkumar, Min Sung Kim, Kwon Taek Lim, and Yeon Tae Jeong. "2,4-Bis(2-chlorophenyl)-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 64, no. 8 (July 26, 2008): o1586. http://dx.doi.org/10.1107/s160053680802268x.

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19

Sliter, Brian, Jessica Morgan, and Arthur Greenberg. "1-Azabicyclo[3.3.1]nonan-2-one: Nitrogen Versus Oxygen Protonation." Journal of Organic Chemistry 76, no. 8 (April 15, 2011): 2770–81. http://dx.doi.org/10.1021/jo200195a.

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20

Park, Dong Ho, V. Ramkumar, and P. Parthiban. "2,4-Bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 68, no. 12 (November 3, 2012): o3282. http://dx.doi.org/10.1107/s1600536812044856.

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21

Parthiban, P., V. Ramkumar, Min Sung Kim, Se Mo Son, and Yeon Tae Jeong. "2,4-Bis(2-bromophenyl)-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 64, no. 12 (November 20, 2008): o2385. http://dx.doi.org/10.1107/s1600536808037501.

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22

Parthiban, P., V. Ramkumar, and Yeon Tae Jeong. "2,4-Bis(2-fluorophenyl)-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (June 17, 2009): o1596. http://dx.doi.org/10.1107/s1600536809022065.

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23

Sundararajan, G., D. Rajaraman, S. Bharanidharan, and K. Krishnasamy. "Synthesis, Spectral and Computational Studies of some 2-(2-(3-Methyl-2,4-Diphenyl-3-Azabicyclo[3.3.1]Nonan-9-Ylidene)Hydrazinyl)Benzo[d]Thiazole Derivatives." International Letters of Chemistry, Physics and Astronomy 61 (November 2015): 28–37. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.61.28.

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A series of some 2-(2-(3-methyl-2,4-diphenyl-3-azabicyclo [3.3.1] nonan-9-ylidene) hydrazinyl) benzo [d] thiazole derivatives 11-14 have been synthesized using acetic acid as the catalyst. All the synthesized compounds were characterized by FT-IR, 1H 13C NMR and HSQC spectral analysis. The molecular modelling was carried out for compound 11 by Gaussian 03W package and its HOMO–LUMO, Mulliken atomic charges, Molecular electrostatic potential (MEP), Hyperpolarizability, Thermodynamic propeties and Natural bond orbital (NBO) analysis were discussed

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24

Sundararajan, G., D. Rajaraman, S. Bharanidharan, and K. Krishnasamy. "Synthesis, Spectral and Computational Studies of some 2-(2-(3-Methyl-2,4-Diphenyl-3-Azabicyclo[3.3.1]Nonan-9-Ylidene)Hydrazinyl)Benzo[d]Thiazole Derivatives." International Letters of Chemistry, Physics and Astronomy 61 (November 3, 2015): 28–37. http://dx.doi.org/10.56431/p-8zh2wc.

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A series of some 2-(2-(3-methyl-2,4-diphenyl-3-azabicyclo [3.3.1] nonan-9-ylidene) hydrazinyl) benzo [d] thiazole derivatives 11-14 have been synthesized using acetic acid as the catalyst. All the synthesized compounds were characterized by FT-IR, 1H 13C NMR and HSQC spectral analysis. The molecular modelling was carried out for compound 11 by Gaussian 03W package and its HOMO–LUMO, Mulliken atomic charges, Molecular electrostatic potential (MEP), Hyperpolarizability, Thermodynamic propeties and Natural bond orbital (NBO) analysis were discussed

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25

Atroshchenko, Yu M., E. G. Nikiforova, I. V. Shakhkel'dyan, Yu D. Grudtsyn, N. G. Akhmedov, E. N. Alifanova, O. Ya Borbulevich, O. V. Shishkin, S. S. Gitis, and A. Ya Kaminskii. "ChemInform Abstract: 3-Azabicyclo[3.3.1]nonane Derivatives. Part 2. Synthesis of 6(7)-R-3-(2-Hydroxyethyl)-1,5-dinitro-3-azabicyclo[3.3.1]non-6-enes." ChemInform 32, no. 4 (January 23, 2001): no. http://dx.doi.org/10.1002/chin.200104182.

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26

Park, Dong Ho, V. Ramkumar, and P. Parthiban. "Crystal structure of 2,4-bis(2-chlorophenyl)-7-tert-pentyl-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 70, no. 11 (October 15, 2014): o1161—o1162. http://dx.doi.org/10.1107/s160053681402176x.

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The title compound, C25H29Cl2NO, which is a chloro analog of 2,4-bis(2-bromophenyl)-7-(tert-pentyl)-3-azabicyclo[3.3.1]nonan-9-one [Park, Ramkumar & Parthiban (2012).Acta Cryst.E68, o2946], exists in a twin-chair conformation with an equatorial orientation of the 2-chlorophenyl groups. Thetert-pentyl group on the cyclohexanone adopts an exocyclic equatorial position and is disordered between two orientations in a ratio 0.520 (8):0.480 (8). The crystal packing shows no directional contacts beyond van der Waals contacts.

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27

Mukhtorov, Loik G., Evgenia V. Ivanova, Maria B. Nikishina, Irina V. Shahkeldyan, Yury M. Atroshchenko, Makhmadkul B. Karimov, and Konstantin I. Kobrakov. "Synthesis and structure of new derivatives of 2-chloro-N-(3-R-1,5-dinitro-8-oxo-3-azabicyclo[3.3.1]non-6-en-7-yl)acetamides." Butlerov Communications 57, no. 3 (March 31, 2019): 83–88. http://dx.doi.org/10.37952/roi-jbc-01/19-57-3-83.

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The production of new 3-azabicyclononane derivatives is an important trend in the synthesis of organic compounds. It is known that 3-azabicyclononane is a key pharmacophore of a number of plant alkaloids that are widely used in medicine (aconitin, quinidine, tropane, cocaine, garnet, etc.). Among synthetic heterocycles containing a 3-azabicyclo[3.3.1]nonane fragment, compounds with various types of biological activity were found: analgesic and anti-inflammatory, antimicrobial and fungicidal, anti-cancer, antioxidant, etc. We synthesized a number of new derivatives of 3-azabicyclo[3.3. 1]nonane by Mannich condensation of hydride σ-adduct 2-chloro-N-(2-hydroxy-3,5-dinitrophenyl)acetamide with formaldehyde and primary amines or amino acids. The synthesis was carried out in two stages. In the first stage, under the action of sodium tetrahydride borate on a solution of 2-chloro-N-(2-hydroxy-3,5-dinitrophenyl)acetamide, the C=C bonds of the aromatic ring were reduced to form a 3-charge hydride adduct. The resulting diaduct was isolated from the solution and, while cooling with ice, was introduced into Mannich condensation with formaldehyde and a solution of the primary amine or amino acid. When the reaction mixture was acidified with dilute orthophosphoric acid to pH 4-5, precipitates of the target products precipitated. After recrystallization from ethanol, the yield of the target products, depending on the substituent at the nitrogen atom, was 75-90%. This method is distinguished by relative simplicity, availability of reagents and allows under mild conditions to transfer from the aromatic system activated by nitro groups to 3-azabicyclo[3.3.1]nonane derivatives, containing promising from the point of view of further functionalization nitro, carbonyl, amino groups, and also halogen atom . The structure of the compounds obtained was proved by IR, 1H-, 13C-, two-dimensional correlation NMR spectroscopy, as well as high-resolution mass spectrometry data (HRMS).

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28

Hulme, Ashley T., Philippe Fernandes, Alastair Florence, Andrea Johnston, and Kenneth Shankland. "Powder study of 3-azabicyclo[3.3.1]nonane-2,4-dione form 2." Acta Crystallographica Section E Structure Reports Online 62, no. 7 (June 28, 2006): o3046—o3048. http://dx.doi.org/10.1107/s1600536806023312.

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A polycrystalline sample of a new polymorph of the title compound, C8H11NO2, was produced during a variable-temperature X-ray powder diffraction study. The crystal structure was solved at 1.67 Å resolution by simulated annealing from laboratory powder data collected at 250 K. Subsequent Rietveld refinement yielded an R wp of 0.070 to 1.54 Å resolution. The structure contains two molecules in the asymmetric unit, which form a C 2 2(8) chain motif via N—H...O hydrogen bonds.

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29

Parthiban, P., V. Ramkumar, and Yeon Tae Jeong. "2,4-Bis(2-methylphenyl)-3-azabicyclo[3.3.1]nonan-9-oneO-methyloxime." Acta Crystallographica Section E Structure Reports Online 66, no. 11 (October 30, 2010): o2978. http://dx.doi.org/10.1107/s1600536810043436.

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30

Asaoka, Morio, Naoto Ohkura, Masaru Yokota, Syuzo Sonoda, and Hisashi Takei. "A New Synthetic Route to Functionalized 2-Azabicyclo[2.2.2]octane." HETEROCYCLES 38, no. 11 (1994): 2455. http://dx.doi.org/10.3987/com-94-6872.

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31

Reed, Damon D., and Stephen C. Bergmeier. "A Facile Synthesis of a Polyhydroxylated 2-Azabicyclo[3.2.1]octane." Journal of Organic Chemistry 72, no. 3 (February 2007): 1024–26. http://dx.doi.org/10.1021/jo0619231.

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32

Chung, John Y. L., and Guo-Jie Ho. "ChemInform Abstract: An Improved Preparation of 2-Azabicyclo[2.2.2]octane." ChemInform 33, no. 48 (May 18, 2010): no. http://dx.doi.org/10.1002/chin.200248158.

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33

Bulygina, Ludmila A., Natalya S. Khrushcheva, Konstantin A. Lyssenko, and Aleksander S. Peregudov. "5,6-Membered CNN palladium pincer complexes of 3-benzyl-8-dimethylamino -3-azabicyclo[3.2.1]octane and 3-benzyl-9-dimethylamino-3-azabicyclo[3.3.1]nonane." Journal of Organometallic Chemistry 887 (May 2019): 64–70. http://dx.doi.org/10.1016/j.jorganchem.2019.02.017.

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34

Lima, Dimas J. P., Antonio E. G. Santana, Michael A. Birkett, and Ricardo S. Porto. "Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine." Beilstein Journal of Organic Chemistry 17 (January 5, 2021): 28–41. http://dx.doi.org/10.3762/bjoc.17.4.

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The 9-azabicyclo[3.3.1]nonane ring system is present in several insect- and plant-derived alkaloids. (−)-Adaline (1) and (+)-euphococcinine (2), found in secretions of Coccinelid beetles, and (+)-N-methyleuphococcinine (3), isolated from the Colorado blue spruce Picea pungens, are members of this alkaloid family. Their unique bicyclic system with a quaternary stereocenter, and the potent biological activity exerted by these homotropane alkaloids, make them attractive synthetic targets. This work aims briefly to review the chemical ecology of Adalia bipunctata and the recent methodologies to obtain adaline (1), euphococcinine (2), and N-methyleuphococcinine (3).

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35

BONJOCH, J., N. CASAMITJANA, J. GRACIA, M. C. UBEDA, and J. BOSCH. "ChemInform Abstract: Functionalized 2-Azabicyclo(3.3.1)nonanes. Part 13. The Fischer Indolization of 2-Azabicyclo(3.3.1)nonan-7-ones. A New Entry to the Dasycarpidan Ring System." ChemInform 22, no. 7 (August 23, 2010): no. http://dx.doi.org/10.1002/chin.199107166.

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36

JEYARAMAN, R., and S. PONNUSWAMY. "ChemInform Abstract: Stereochemistry of N-Acetyl-r-2,c-4-diphenyl-3-azabicyclo[3.3.1]nonanes and N-Ethoxycarbonyl-r-2,c-4-diphenyl-3-azabicyclo[3.3.1]nonane." ChemInform 29, no. 15 (June 23, 2010): no. http://dx.doi.org/10.1002/chin.199815020.

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37

Kollár, László, Ádám Erdélyi, Haroon Rasheed, and Attila Takács. "Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation." Molecules 26, no. 6 (March 23, 2021): 1813. http://dx.doi.org/10.3390/molecules26061813.

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The aminocarbonylation of various alkenyl and (hetero)aryl iodides was carried out using tropane-based amines of biological importance, such as 8-azabicyclo[3.2.1]octan-3-one (nortropinone) and 3α-hydroxy-8-azabicyclo[3.2.1]octane (nortropine) as N-nucleophile. Using iodoalkenes, the two nucleophiles were selectively converted to the corresponding amide in the presence of Pd(OAc)2/2 PPh3 catalysts. In the presence of several iodo(hetero)arenes, the application of the bidentate Xantphos was necessary to produce the target compounds selectively. The new carboxamides of varied structure, formed in palladium-catalyzed aminocarbonylation reactions, were isolated and fully characterized. In this way, a novel synthetic method has been developed for the producing of N-acylnortropane derivatives of biological importance.

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38

Ahlenstiel, Eckart, Wolfgang Kliegel, Steven J. Rettig, and James Trotter. "Structural studies of organoboron compounds. LVII. Synthesis and structure of bicyclic boron-nitrogen betaines. 1-Methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]octane." Canadian Journal of Chemistry 71, no. 2 (February 1, 1993): 263–71. http://dx.doi.org/10.1139/v93-038.

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The syntheses and structures of the bicyclic boron-nitrogen betaines 1-methyl-5-(3-nitrophenyl)-4,6,9-trioxa-1-azonia-5-boratabicyclo[3.3.1]nonane, 7a, and 3,3,4-trimethyl-1-(3-nitrophenyl)-2,6,7-trioxa-3-azonia-1-boratabicyclo[2.2.2]-octane, 14a, are reported. Crystals of 7a are orthorhombic, a = 20.256(2), b = 37.652(2), c = 6.642(1) Å, Z = 16, space group Fdd2, and those of 14a are orthorhombic, a = 21.402(2), b = 11.334(3), c = 11.248(2) Å, Z = 8, space group Pbca. The structures were solved by direct methods and were refined by full-matrix least-squares procedures to R = 0.038 and 0.045 (Rw = 0.036 and 0.053) for 975 and 1646 reflections with I ≥ 3σ(F2), respectively. The X-ray analyses establish the bicyclo[3.3.1]nonane and bicyclo[2.2.2]octane "cage" structures for 7a and 14a, respectively. Bond lengths involving the tetrahedral boron atom are (N)O—B = 1.519(5), (C)O—B = 1.444(6) and 1.443(6), C(aryl)—B = 1.602(5) Å for 7a; and (N)O—B = 1.530(3), (C)O—B = 1.446(3) and 1.455(3), C(aryl)—B = 1.608(3) Å for 14a. Weak [Formula: see text] interactions are the main feature of the crystal packing arrangements of both compounds.

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39

Parthiban, P., V. Ramkumar, Dong Ho Park, and Yeon Tae Jeong. "2,4-Bis(2-ethoxyphenyl)-7-methyl-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 67, no. 6 (May 20, 2011): o1475—o1476. http://dx.doi.org/10.1107/s1600536811018472.

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40

Parthiban, P., V. Ramkumar, and Yeon Tae Jeong. "1-Methyl-2,4-bis(2-methoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 65, no. 12 (November 18, 2009): o3103. http://dx.doi.org/10.1107/s1600536809047928.

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41

Parthiban, P., V. Ramkumar, and Yeon Tae Jeong. "2,4-Bis(2-fluorophenyl)-1-methyl-3-azabicyclo[3.3.1]nonan-9-one." Acta Crystallographica Section E Structure Reports Online 66, no. 1 (December 19, 2009): o194—o195. http://dx.doi.org/10.1107/s1600536809053677.

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42

Amat, Mercedes, Enric Sanfeliu, Josep Bonjoch, and Joan Bosch. "Synthesis of 2-azabicyclo[3.3.1]nonan-3,7-diones and their fischer indolization." Tetrahedron Letters 30, no. 29 (January 1989): 3841–44. http://dx.doi.org/10.1016/s0040-4039(01)80673-0.

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43

Quirante, Josefina, Mercè Torra, Faı̈za Diaba, Carmen Escolano, and Josep Bonjoch. "Synthesis of enantiopure 2-azabicyclo[3.3.1]nonanes by a radical ring closure." Tetrahedron: Asymmetry 10, no. 12 (June 1999): 2399–410. http://dx.doi.org/10.1016/s0957-4166(99)00221-9.

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44

Adembri, Giorgio, Donato Donati, Stefania Fusi, and Fabio Ponticelli. "2-Azabicyclo[4.2.0]octane derivatives: stereoselective photochemical synthesis and chemical reactivity." Journal of the Chemical Society, Perkin Transactions 1, no. 15 (1992): 2033. http://dx.doi.org/10.1039/p19920002033.

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45

Wauters, Iris, Ann De Blieck, Koen Muylaert, Thomas S. A. Heugebaert, and Christian V. Stevens. "Synthesis of Epibatidine Analogues Having a 2-Substituted 2-Azabicyclo[2.2.2]octane Skeleton." European Journal of Organic Chemistry 2014, no. 6 (December 17, 2013): 1296–304. http://dx.doi.org/10.1002/ejoc.201301397.

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46

Bhatti, Balwinder S., Jon-Paul Strachan, Scott R. Breining, Craig H. Miller, Persida Tahiri, Peter A. Crooks, Niranjan Deo, Cynthia S. Day, and William S. Caldwell. "Synthesis of 2-(Pyridin-3-yl)-1-azabicyclo[3.2.2]nonane, 2-(Pyridin-3-yl)-1-azabicyclo[2.2.2]octane, and 2-(Pyridin-3-yl)-1-azabicyclo[3.2.1]octane, a Class of Potent Nicotinic Acetylcholine Receptor–Ligands." Journal of Organic Chemistry 73, no. 9 (May 2008): 3497–507. http://dx.doi.org/10.1021/jo800028q.

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47

Moriguchi, Tetsuji, Suvratha Krishnamurthy, Toru Arai, Taisuke Matsumoto, Koji Araki, Akihiko Tsuge, and Norikazu Nishino. "Synthesis and Molecular Structure of tert-Butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate." Journal of Crystallography 2014 (August 17, 2014): 1–6. http://dx.doi.org/10.1155/2014/645079.

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The compound tert-butyl 3-oxo-2-oxa-5-azabicyclo[2.2.2]octane-5-carboxylate was synthesized as a cyclic amino acid ester from the corresponding ethyl 2-amino-4-(2-oxiranyl)butanoate HCl salt via an intramolecular lactonization reaction and was characterized by using 1H NMR spectroscopy and high-resolution mass spectrometry. The product was then recrystallized from dichloromethane/diethyl ether and its structure was determined via single crystal X-ray diffraction analysis. The crystal was found to be of the monoclinic space group P21/c (no. 14) with a = 10.217(2) Å, b = 11.676(3) Å, c = 10.273(3) Å, β = 114.186(13)°, and Dcalc = 1.350 g/cm3 at 123 K. The compound has bicyclo[2.2.2]octane structure including a lactone moiety and a piperidine ring, and the two diastereomers of the molecules are present in a 1 : 1 ratio in the crystal.

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48

Carroll, F. Ivy, Philip Abraham, J. Bruce Pitner, S. D. Jablonski, P. Singh, Yong Wha Kwon, and David J. Triggle. "A new synthesis and crystal structure of 2-methyl-2-azabicyclo[3.3.1]nonan-7α-ol." J. Chem. Soc., Chem. Commun., no. 10 (1992): 795–96. http://dx.doi.org/10.1039/c39920000795.

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49

Ramachandran, R., M. Rani, and S. Kabilan. "2-(2,4-Diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidenehydrazono)-1,3-thiazolidin-4-one." Acta Crystallographica Section E Structure Reports Online 65, no. 3 (February 25, 2009): o584. http://dx.doi.org/10.1107/s1600536809005339.

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50

Priya, K., K. Saravanan, S. Kabilan, and S. Selvanayagam. "Crystal structure of 2-(2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-ylidene)acetonitrile." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (September 26, 2015): o792—o793. http://dx.doi.org/10.1107/s2056989015017740.

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In the title 3-azabicyclononane derivative, C22H22N2, both the fused piperidine and cyclohexane rings adopt a chair conformation. The phenyl rings attached to the central azabicylononane fragment in an equatorial orientation are inclined to each other at 23.7 (1)°. The amino group is not involved in any hydrogen bonding, so the crystal packing is stabilized only by van der Waals forces.

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