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Relevant bibliographies by topics / Azabicyclo[3.2.1]octanes

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Academic literature on the topic 'Azabicyclo[3.2.1]octanes'

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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Journal articles on the topic "Azabicyclo[3.2.1]octanes"

1

Armstrong, Ian, and Stephen Bergmeier. "Development of a Method for the Synthesis of 4-Aryl-Functionalized 2-Azabicyclo[3.2.1]octanes." Synthesis 49, no. 12 (2017): 2733–42. http://dx.doi.org/10.1055/s-0036-1558973.

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A method for the synthesis of 4-substituted azabicyclo[3.2.1]octanes from N-tosyl-2-azabicyclo[3.2.1]octa-3,6-diene, a versatile bicyclic heterocycle not commonly used in medicinal chemistry research, is presented. The method uses bromination, followed by Suzuki coupling, and subsequent reduction and deprotection. The desired 4-substituted azabicyclo[3.2.1]octanes were obtained in moderate to high yields.

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Ghosh, Shyamali, William A. Kinney, Diane A. Gauthier, Edward C. Lawson, Tomas Hudlicky, and Bruce E. Maryanoff. "Convenient preparation of aryl-substituted nortropanes by SuzukiMiyaura methodology." Canadian Journal of Chemistry 84, no. 4 (2006): 555–60. http://dx.doi.org/10.1139/v06-045.

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The synthesis of a new bicyclic vinyl boronate (5) was accomplished from N-Boc-nortropinone (6) in two steps. The SuzukiMiyaura coupling of 5 to a variety of aryl bromides and triflates afforded 3-aryl-8-azabicyclo[3.2.1]oct-2-enes in good yields by adjusting the substrate and (or) reaction conditions. Reduction to the 3-aryl-8-azabicyclo[3.2.1]octanes was achieved by hydrogenation. Interestingly, the coupling was also successful with benzyl bromides, providing entry into another group of intermediates.Key words: nortropane, SuzukiMiyaura, boronate, piperidine, GPCR, benzyl bromide.

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Baylis, Alison M., and Eric J. Thomas. "Aspects of the chemistry of 8-azabicyclo[3.2.1]octanes." Tetrahedron 63, no. 47 (2007): 11666–71. http://dx.doi.org/10.1016/j.tet.2007.08.109.

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Davies, Huw M. L., Pingda Ren, Norman Kong, Tammy Sexton та Steven R. Childers. "Synthesis and monoamine transporter affinity of 3β-(4-(2-pyrrolyl)phenyl)-8-azabicyclo[3.2.1]octanes and 3β-(5-Indolyl)-8-azabicyclo[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters 11, № 4 (2001): 487–89. http://dx.doi.org/10.1016/s0960-894x(00)00701-0.

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Masschelein, Kurt G. R., Christian V. Stevens, Nicolai Dieltiens, and Diederica D. Claeys. "Exploiting the regioselectivity of pyroglutamate alkylations for the synthesis of 6-azabicyclo[3.2.1]octanes and 4-azabicyclo[3.3.0]octanes." Tetrahedron 63, no. 22 (2007): 4712–24. http://dx.doi.org/10.1016/j.tet.2007.03.084.

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Davies, Huw M. L., Pingda Ren, Norman Kong, Tammy Sexton та Steven R. Childers. "ChemInform Abstract: Synthesis and Monoamine Transporter Affinity of 3β-(4-(2-Pyrrolyl)phenyl)-8-azabicyclo[3.2.1]octanes and 3β-(5-Indolyl)-8-azabicyclo[3.2.1]octanes." ChemInform 32, № 24 (2010): no. http://dx.doi.org/10.1002/chin.200124154.

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Quirante, Josefina, Xavier Vila, Josep Bonjoch, Alan P. Kozikowski, and Kenneth M. Johnson. "2,3-Disubstituted 6-azabicyclo[3.2.1]octanes as novel dopamine transporter inhibitors." Bioorganic & Medicinal Chemistry 12, no. 6 (2004): 1383–91. http://dx.doi.org/10.1016/j.bmc.2004.01.019.

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8

Pulipaka, Aravinda B., and Stephen C. Bergmeier. "A Synthesis of 6-Azabicyclo[3.2.1]octanes. The Role ofN-Substitution." Journal of Organic Chemistry 73, no. 4 (2008): 1462–67. http://dx.doi.org/10.1021/jo702444c.

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Casavant, Barbara J., Azade S. Hosseini, and Sherry R. Chemler. "ChemInform Abstract: 6-Azabicyclo[3.2.1]octanes via Copper-Catalyzed Enantioselective Alkene Carboamination." ChemInform 46, no. 7 (2015): no. http://dx.doi.org/10.1002/chin.201507143.

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10

Tamiz, Amir P., Miles P. Smith, Istvan Enyedy, et al. "Synthesis and biological evaluation of 1-azabicyclo-[3.2.1]octanes: new dopamine transporter inhibitors." Bioorganic & Medicinal Chemistry Letters 10, no. 15 (2000): 1681–86. http://dx.doi.org/10.1016/s0960-894x(00)00308-5.

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Dissertations / Theses on the topic "Azabicyclo[3.2.1]octanes"

1

Pulipaka, Aravinda B. "Intramolecular Ring Opening Reactions of Aziridines by π-Nucleophiles". Ohio University / OhioLINK, 2008. http://rave.ohiolink.edu/etdc/view?acc_num=ohiou1205514895.

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2

Claret, François. "Synthèse et réactivité de 3,4,6,7-tétraméthylidène-bicyclo (3.2.1)octanes 2,8-disubstitués /." Lausanne, 1992. http://library.epfl.ch/theses/?nr=1005.

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Saint-Dizier, Alexandre Christian Claude. "Samarium diiodide mediated cascade radical cyclisations of methylenecyclopropane derivatives : synthesis of bicyclo-[3.2.1]-octanes." Thesis, University of Southampton, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.395912.

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Filippini, Marie-Hélène. "Nouvelles réactions domino anioniques : préparation stéréosélective de bicyclo[3.2.1]octanes et de cycloheptanes fonctionnalisés." Aix-Marseille 3, 1996. http://www.theses.fr/1996AIX30065.

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Au cours de ce travail, nous avons developpe de nouvelles reactions domino anioniques, basees sur la reactivite d'anions stabilises, dans le but de construire stereoselectivement des squelettes bicyclo3. 2. 1octaniques et des cycloheptanes fonctionnalises. Ces sequences en cascade font intervenir des reactions simples et repondent de facon satisfaisante aux trois criteres fondamentaux de selectivite, d'accessibilite et de proprete. L'etude detaillee de la reaction de carbocyclisation entre une cyclopentanone -carbonylee et des aldehydes ,-insatures a montre l'efficacite de cette approche pour la construction stereoselective de systemes bicyclo3. 2. 1octaniques polyfonctionnalises. Ces derives se sont averes etre des intermediaires de synthese particulierement attrayants pour l'acces au squelette cycloheptanique, apres une fragmentation selective selon une reaction de retro-dieckmann. Cette reactivite nous a permis de mettre au point la cascade mardi qui constitue une nouvelle reaction d'extension de cycle a deux atomes de carbone particulierement efficace. La sequence est initiee par une addition de michael, suivie d'une aldolisation intramoleculaire conduisant aux intermediaires 2-hydroxybicyclo3. 2. 1octane. Ces derniers evoluent in situ par une reaction de retro-dieckmann vers la formation stereoselective de derives cycloheptaniques possedant jusqu'a cinq centres stereogenes. Dans le cas d'aldehydes ,-insatures -substitues, la cascade mardi est suivie d'une deshydratation et d'une saponification chimioselective restituant diastereoselectivement des cycloheptenes trisubstitues. Cette evolution particuliere constitue un exemple representatif de l'efficacite d'une reaction domino qui fait intervenir ici une suite de cinq reactions differentes

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Chang, Yi-Mei, and 張依湄. "Lewis acid-Promoted Intramolecular Cyclization Reaction of Six-Member Ring 4-Ene- and 1-Yne-Ynamides： Synthesis of 6-Azabicyclo[3.2.1]octanes, Spiro[3.5]nonanes, and Isoquinolines." Thesis, 2017. http://ndltd.ncl.edu.tw/handle/y4x2du.

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碩士<br>國立臺灣師範大學<br>化學系<br>105<br>Abstract This dissertation covered Lewis acid-promoted intramolecular cyclization reactions of six-membered ring 4-ene- and 1-yne-ynamides afforded 6-azabicyclo[3.2.1]octane, spiro[3.5]nonane, and isoquinoline derivatives. （1） The aluminum(III) chloride-promoted cyclization/chlorination of six-membered ring 4-(N-ethynylamino)cyclohexene enabled a straight forward approach to the 6-azabicyclo[3.2.1]octane. Acid treatment of the resultant chlorinated arylideneazabicyclooctanes furnished 3-alkanoyl-4-chlorocyclohex anamines in excellent yields and high stereoselectivity. （2） The iron(III) bromide-promoted cyclization of six-membered ring 1-yneynamides provided brominated spiro[3.5]nonane derivatives. The reaction mechanism was suggested to proceed via rearrangement of N-keteniminium ion to C-ketenimine followed by cyclization of C-ketenimine generated spiro[3.5]nonane derivatives. The reaction had several advantages: easily available starting materials, inexpensive iron (III) bromide, and short reaction times. （3） The gold (I)-catalyzed intramolecular cyclization of 1-[2-(N-tosyl-N-phenylethynylethyl)]cyclohexene afforded isoquinoline derivatives in fair good yields. The reactions were procedurally simple, efficient, producing isoquinolines under mild reaction conditions. Keywords： Lewis acid, aluminum(III) chloride, iron(III) bromide, enynamides, 1-yneynamides, azabicyclo[3.2.1]octane, spiro[3.5]nonane, isoquinoline

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Chang, Chihyi, and 張之頤. "Study on the rearrangement of Camphor-derivedalkyl [3.2.1]bicyclic alcohols to dimethyl alkyl[2.2.2]bicyclic octanes." Thesis, 2012. http://ndltd.ncl.edu.tw/handle/26297390456215178429.

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碩士<br>國立暨南國際大學<br>應用化學系<br>100<br>Addition reation of Camphor derived [3.2.1]bicyclic hydroxy ketone with alkyl organic lithium compound and Grignard reagent to give Camphor derived [3.2.1] bicyclic diol compound, and then the acetalization generated the acetyl alcohol product. Then, rearrangement of various types of [3.2.1]bicyclic acetyl alcohol is catalyzed by the catalytic amount of p-toluenesulfonic acid and generated camphor molecule derived [2.2.2]bicyclic product. Then, this camphor molecule derived [2.2.2]bicyclic acetyl compound soluble in methanol reacted with sodium hydroxide to give the camphor molecule derived [2.2.2]bicyclic secondary alcohol compound product. Then camphor molecule derived [2.2.2]bicyclo secondary alcohol compound are oxidized to camphor molecule derived [2.2.2]bicyclo ketone. This compound is further oxidized to camphor molecule derived [2.2.2]bicyclo dione product by selenium dioxide in acetic acid, Finally, reaction of the dione compound with lead acetate in methanol generated ring-opening methylene-dimethyl-cyclohexane diesters derivatives, the methylene-dimethyl-cyclo hexane diesters containing two stereocenters.

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Book chapters on the topic "Azabicyclo[3.2.1]octanes"

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Whitesell, James K., and Mark A. Minton. "Bicyclo[3.2.1]octanes." In Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy. Springer Netherlands, 1987. http://dx.doi.org/10.1007/978-94-009-3161-9_11.

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2

Ellenbroek, Bart, Alfonso Abizaid, Shimon Amir, et al. "Endo-3-(Diphenylmethoxy)-8-Methyl-8-Azabicyclo[3.2.1]Octane Methanesulfonate." In Encyclopedia of Psychopharmacology. Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/978-3-540-68706-1_4235.

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3

Morgan, Michael M., MacDonald J. Christie, Thomas Steckler, et al. "Methyl (1R,2R,3S,5S)-3-(Benzoyloxy)-8-Methyl-8-Azabicyclo[3.2.1] Octane-2-Carboxylate." In Encyclopedia of Psychopharmacology. Springer Berlin Heidelberg, 2010. http://dx.doi.org/10.1007/978-3-540-68706-1_3393.

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4

Block, E. "Ring-Opening Reactions of Thiaoxabicyclo[3.2.1]octanes and Thiaoxabicyclo[3.3.1]nonanes." In Ene-X Compounds (X=S, Se, Te, N, P). Georg Thieme Verlag KG, 2007. http://dx.doi.org/10.1055/sos-sd-033-00338.

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5

"Cocaine (3-benzoyloxy)-8methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid methyl ester)." In Encyclopedia of Genetics, Genomics, Proteomics and Informatics. Springer Netherlands, 2008. http://dx.doi.org/10.1007/978-1-4020-6754-9_3242.

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6

Lambert, Tristan H. "C–O Ring Construction: The Reisman Synthesis of (–)-Acetylaranotin." In Organic Synthesis. Oxford University Press, 2015. http://dx.doi.org/10.1093/oso/9780190200794.003.0048.

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The Prins cyclization is a powerful approach for the construction of oxygen-containing heterocycles. B.V. Subba Reddy at the Indian Institute of Technology has reported (Tetrahedron Lett. 2012, 53, 3100) an approach to 2,6-dioxabicyclo[3.2.1]octanes 2 by way of a tandem Prins reaction/intramolecular acetalization of the diol 1 and a variety of aldehydes. Christine L. Willis of the University of Bristol utilized (Angew. Chem. Int. Ed. 2012, 51, 3901) nontraditional γ, δ-unsaturated alcohols 3 for a Prins-type strategy to access bicyclic heterocycles 5, while Zhenlei Song of Sichuan University employed (Angew. Chem. Int. Ed. 2012, 51, 5367) a bis(silyl) homoallylic alcohol 7 in the synthesis of structures such as 8, corresponding to the B ring of the bryostatins. In a mechanistically related process, the conversion of unsaturated ketones 9 to tetrahydropyranyl products 11 by treatment with a boronic acid 10 and triflic anhydride was described (Org. Lett. 2012, 14, 1187) by Aurelio G. Csáky at the Universidad Complutense in Spain. A powerful approach to heterocycles is via the ring expansion of smaller, and especially strained, ring systems. Jon T. Njardarson of the University of Arizona has been exploring such strategies and has reported (Angew. Chem. Int. Ed. 2012, 51, 5675) the conversion of vinyl oxetanes to dihydropyrans via catalysis by transition metals or Brønsted acids. The use of a chiral catalyst such as 13 allowed for the enantioselective conversion of divinyl oxetane 12 to enantioenriched dihydropyran 14. Meanwhile, Amir H. Hoveyda at Boston College and Richard R. Schrock at MIT have developed (J. Am. Chem. Soc. 2012, 134, 2788) a highly reactive and stereoselective catalyst for the ring-opening/cross-metathesis of several ring systems such as 15 with enol ethers. Notably, reactions occur rapidly (e.g., 10 min) using as little as 0.15 mol% catalyst. An alkynyl cyclopropyl ketone such as 17 can be converted (Angew. Chem. Int. Ed. 2012, 51, 4112) to products 18 by treatment with a gold/silver catalyst mixture, as shown by Zhongwen Wang at Nankai University. Notably, the oxabicyclic ring structure contained within 18 is present in a diversity of natural product structures.

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Conference papers on the topic "Azabicyclo[3.2.1]octanes"

1

Eggimann, Thomas, and Hal Wieser. "Vibrational-circular-dichroism spectra of five methyl-substituted 6,8-dioxabicyclo[3.2.1]octanes." In Luebeck - DL tentative, edited by Herbert M. Heise, Ernst H. Korte, and Heinz W. Siesler. SPIE, 1992. http://dx.doi.org/10.1117/12.56402.

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