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

Author: Grafiati

Published: 4 June 2021

Last updated: 3 February 2022

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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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2

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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3

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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4

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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5

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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6

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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7

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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9

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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11

Meltzer, Peter C., Mark McPhee, and Bertha K. Madras. "Synthesis and biological activity of 2-Carbomethoxy-3-catechol-8-azabicyclo[3.2.1]octanes." Bioorganic & Medicinal Chemistry Letters 13, no. 22 (2003): 4133–37. http://dx.doi.org/10.1016/j.bmcl.2003.07.014.

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12

Bradley, Amy L., Sari Izenwasser, Dean Wade, Shaine Cararas, and Mark L. Trudell. "Synthesis of dopamine transporter selective 3-{2-(Diarylmethoxyethylidene)}-8-alkylaryl-8-azabicyclo[3.2.1]octanes." Bioorganic & Medicinal Chemistry Letters 13, no. 4 (2003): 629–32. http://dx.doi.org/10.1016/s0960-894x(02)01051-x.

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13

Schmidt, Elena, Ivan Bidusenko, Igor Ushakov, Nadezhda Protsuk, and Boris Trofimov. "An Easy Access to Sulfur Derivatives of 6,8-Dioxabicyclo[3.2.1]octanes, Naturally Abundant Scaffolds." Synthesis 50, no. 13 (2018): 2624–30. http://dx.doi.org/10.1055/s-0036-1591990.

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Sulfur derivatives of 6,8-dioxabicyclo[3.2.1]octanes related to a number of natural products have been synthesized by the click hydrothiolation (AIBN or UV irradiation) of 7-methylene-6,8-dioxabicyclo[3.2.1]octanes, assembled from acetylene and ketones in a one-pot transition-metal-free synthetic operation. An unusual feature of this free-radical reaction is that it is accelerated in the presence of bases due to involvement of the latter in a competition between the thiol addition and proton-catalyzed isomerization of the starting bicyclooctanes.

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14

Bradley, Amy L., Sari Izenwasser, Dean Wade, Cheryl Klein-Stevens, Naijue Zhu та Mark L. Trudell. "Synthesis and dopamine transporter binding affinities of 3α-Benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes". Bioorganic & Medicinal Chemistry Letters 12, № 17 (2002): 2387–90. http://dx.doi.org/10.1016/s0960-894x(02)00464-x.

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15

Tamiz, Amir P., Miles P. Smith, Istvan Enyedy, et al. "ChemInform Abstract: Synthesis and Biological Evaluation of 1-Azabicyclo[3.2.1]octanes: New Dopamine Transporter Inhibitors." ChemInform 31, no. 44 (2000): no. http://dx.doi.org/10.1002/chin.200044172.

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16

He, Chi, Zengbing Bai, Jialei Hu, et al. "A divergent [5+2] cascade approach to bicyclo[3.2.1]octanes: facile synthesis of ent-kaurene and cedrene-type skeletons." Chemical Communications 53, no. 60 (2017): 8435–38. http://dx.doi.org/10.1039/c7cc04292b.

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17

Pikun, Nadiia V., Natalya P. Kolesnyk, Eduard B. Rusanov, et al. "Contrasting reactivity of fluorinated 2,6-heptanediones towards amines and ammonia, leading to cyclohexanediones or 2-oxa-6-azabicyclo[2.2.2]octanes and evaluation of their cytotoxicity." New Journal of Chemistry 43, no. 26 (2019): 10537–44. http://dx.doi.org/10.1039/c9nj01446b.

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18

Jo, Hanbyeol, Ahmed H. E. Hassan, Seung Young Jung, Jae Kyun Lee, Yong Seo Cho, and Sun-Joon Min. "Construction of 8-Azabicyclo[3.2.1]octanes via Sequential DDQ-Mediated Oxidative Mannich Reactions ofN-Aryl Pyrrolidines." Organic Letters 20, no. 4 (2018): 1175–78. http://dx.doi.org/10.1021/acs.orglett.8b00098.

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19

Cheng, Jie, Sari Izenwasser, Chunming Zhang, Suhong Zhang, Dean Wade, and Mark L. Trudell. "Synthesis and nicotinic acetylcholine receptor binding affinities of 2- and 3-isoxazolyl-8-azabicyclo[3.2.1]octanes." Bioorganic & Medicinal Chemistry Letters 14, no. 7 (2004): 1775–78. http://dx.doi.org/10.1016/j.bmcl.2004.01.025.

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20

Schmidt, Elena Yu, Nadezhda V. Semenova, Elena V. Ivanova, et al. "Acetylene-based two-step diastereoselective synthesis of bridgehead dihydro-oxadiazines using ketones and hydrazine as the only reactants." Chemical Communications 55, no. 18 (2019): 2632–35. http://dx.doi.org/10.1039/c9cc00315k.

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Bridgehead dihydro-1,3,4-oxadiazines are synthesized by the acid-catalyzed diastereoselective reaction of hydrazine with 6,8-dioxabicyclo[3.2.1]octanes, the products of the superbase-promoted self-organization of acetylene with ketones.

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21

Hong, Bor-Cherng, and Sheng-Fei Chin. "Bicyclo[3.2.1]octanes via McMurry Couplings." Synthetic Communications 29, no. 18 (1999): 3097–106. http://dx.doi.org/10.1080/00397919908085933.

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22

Perlmutter, Patrick, and Walailak Selajarern. "The NARC-Based Approach to the Enantioselective Synthesis of the Zaragozic Acids. Synthesis of a C 5-Alkoxycarbonyl-Substituted 2,8-Dioxabicyclo[3.2.1]octane." Australian Journal of Chemistry 53, no. 4 (2000): 349. http://dx.doi.org/10.1071/ch00045.

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A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octanes is described. The key process involves a highly stereoselective (NARC) sequence of a nucleophilic addition followed by ring closure.

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23

Cameron, Jenny M. "Donald W. Cameron." Australian Journal of Chemistry 53, no. 4 (2000): 241. http://dx.doi.org/10.1071/ch00063.

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A direct method for the preparation of C 5-alkoxycarbonyl-substituted 2,8-dioxabicyclo[3.2.1]octanes is described. The key process involves a highly stereoselective (NARC) sequence of a nucleophilic addition followed by ring closure.

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24

Weck, Christian, Franziska Obst, Elisa Nauha, Christopher J. Schofield та Tobias Gruber. "Synthesis of a bicyclic oxo-γ-lactam from a simple caprolactam derivative". New Journal of Chemistry 41, № 18 (2017): 9984–89. http://dx.doi.org/10.1039/c7nj02348k.

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25

Liu, Lin, Hai-Long Cheng, Wen-Qiang Ma, et al. "Improved synthesis of 8-oxabicyclo[3.2.1]octanes via tandem C–H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization." Chemical Communications 54, no. 2 (2018): 196–99. http://dx.doi.org/10.1039/c7cc08511g.

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A tandem C–H oxidation/oxa-[3,3] Cope rearrangement/aldol cyclization promoted by T<sup>+</sup>BF<sub>4</sub><sup>−</sup>/ZnBr<sub>2</sub> has been successfully developed allowing the efficient construction of 8-oxabicyclo[3.2.1]octanes.

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26

Su, Xiang, Yihua Sun, Jiannian Yao, Hui Chen, and Chao Chen. "Acid-promoted bicyclization of arylacetylenes to benzobicyclo[3.2.1]octanes through cationic rearrangements." Chemical Communications 52, no. 24 (2016): 4537–40. http://dx.doi.org/10.1039/c6cc00452k.

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Acid-promoted site- and stereo-selective bicyclization of alkynes to benzobicyclo[3.2.1]octanes was realized with atom- and step-economy. The reaction proceeded through two C–C bonds formed on remote alkyl C–H bonds via twice long-distance cationic rearrangement.

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27

Liao, Hongze, Wei-Lin Leng, Kim Le Mai Hoang, et al. "Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals." Chemical Science 8, no. 9 (2017): 6656–61. http://dx.doi.org/10.1039/c7sc02625k.

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A gold-catalyzed tandem 1,3-acyloxy migration/Ferrier rearrangement to access 8-oxabicyclo[3.2.1]octanes with high efficiency and complete diastereoselectivity was developed successfully. Resultant compounds could undergo the interrupted Nazarov cyclization to afford diastereomerically pure 11-oxatricyclo[5.3.1.0]undecanes.

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28

Blunt, John W., Andrew Burritt, James M. Coxon, and Peter J. Steel. "NMR Study of Substituted Bicyclo[3.2.1]octanes." Magnetic Resonance in Chemistry 34, no. 2 (1996): 131–36. http://dx.doi.org/10.1002/(sici)1097-458x(199602)34:2<131::aid-omr846>3.0.co;2-t.

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29

Ievlev, Mikhail Yu, and Oleg V. Ershov. "Synthesis of 2,7-dioxabicyclo[3.2.1]octanes (microreview)." Chemistry of Heterocyclic Compounds 52, no. 4 (2016): 213–15. http://dx.doi.org/10.1007/s10593-016-1864-0.

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30

R. Williams, David, Samarjit Patnaik, and Guillermo S. Cortez. "Studies of Zoanthamine Alkaloids. A General Scheme for the Preparation of Functionalized 8-Oxa-6-azabicyclo[3.2.1]octanes." HETEROCYCLES 72, no. 1 (2007): 213. http://dx.doi.org/10.3987/com-07-s(k)61.

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31

Bradley, Amy L., Sari Izenwasser, Dean Wade, Cheryl Klein-Stevens, Naijue Zhu та Mark L. Trudell. "ChemInform Abstract: Synthesis and Dopamine Transporter Binding Affinities of 3α-Benzyl-8-(diarylmethoxyethyl)-8-azabicyclo[3.2.1]octanes (VIII)." ChemInform 33, № 51 (2010): no. http://dx.doi.org/10.1002/chin.200251159.

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32

Chiou, Wen-Hua, and Hao-Yu Chen. "Synthesis of dendrobatid alkaloid (+)-167B and (+)-209D and the investigation of diastereoselectivity using DFT calculations." RSC Advances 7, no. 2 (2017): 684–87. http://dx.doi.org/10.1039/c6ra24960d.

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33

Grygorenko, Oleksandr, Yevhenii Sokolenko, Eugeniy Ostapchuk, and Artem Artemenko. "An Approach to 3-Oxa-7-azabicyclo[3.3.0]octanes – Bicyclic Morpholine Surrogates." Synthesis 49, no. 14 (2017): 3112–17. http://dx.doi.org/10.1055/s-0036-1588785.

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An approach to 3-oxa-7-azabicyclo[3.3.0]octanes, bicyclic morpholine analogues, is reported, which relies on [3+2] cycloaddition of maleic anhydrides or furan-2(5H)-ones and an in situ generated azomethine ylide. The utility of the method was demonstrated on a multigram scale.

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34

Kollár, László, Ádám Erdélyi, Haroon Rasheed, and Attila Takács. "Selective Synthesis of N-Acylnortropane Derivatives in Palladium-Catalysed Aminocarbonylation." Molecules 26, no. 6 (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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35

Rodriguez, Sandra, Uxue Uria, Efraim Reyes, et al. "Enantioselective construction of the 8-azabicyclo[3.2.1]octane scaffold: application in the synthesis of tropane alkaloids." Organic & Biomolecular Chemistry 19, no. 17 (2021): 3763–75. http://dx.doi.org/10.1039/d1ob00143d.

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The 8-azabicyclo[3.2.1]octane core is the central motif of tropane alkaloids. This review compiles the methodologies employed to synthesize this scaffold in an enantioenriched form from achiral starting materials.

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36

Davies, Huw M. L., Lisa A. Kuhn, Craig Thornley, Julius J. Matasi, Tammy Sexton та Steven R. Childers. "Synthesis of 3β-Aryl-8-azabicyclo[3.2.1]octanes with High Binding Affinities and Selectivities for the Serotonin Transporter Site". Journal of Medicinal Chemistry 39, № 13 (1996): 2554–58. http://dx.doi.org/10.1021/jm9600508.

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37

Bubb, William A. "NMR Characterization of3,6-Dioxa-8-azabicyclo[3.2.1]octanes andN-[Tris(hydroxymethyl)methyl]alanine Formedfrom Methylglyoxal in Tris Buffer Solutions." Magnetic Resonance in Chemistry 35, no. 3 (1997): 191–98. http://dx.doi.org/10.1002/(sici)1097-458x(199703)35:3<191::aid-omr54>3.0.co;2-c.

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38

Bouab, Otmane, Gérard Lamaty, and Claude Moreau. "Synthèse et hydrolyse d'orthoesters trioxa-2,7,8 bicyclo[3.2.1] octanes et trioxa-2,8,9 bicyclo[3.3.1] nonanes." Canadian Journal of Chemistry 63, no. 4 (1985): 816–22. http://dx.doi.org/10.1139/v85-135.

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The rates of hydrolysis of 1-substituted 2,7,8-trioxabicyclo[3.2.1]octanes and 2,8,9-trioxabicyclo[3.3.1]nonanes (R = H, CH3, C6H5) have been determined at two temperatures in dioxan/water (60:40 by volume). These new results confirm the behaviour generally observed in the hydrolysis of orthoesters which have a favourable conformation to hydrolyze under stereoelectronic control.

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39

Davies, Huw M. L., and Guoan Cao. "Cation induced rearrangement of 8-azabicyclo[3.2.1]octa-2,6-dienes to 6-azabicyclo[3.2.1]oct-2-enes." Tetrahedron Letters 39, no. 33 (1998): 5943–46. http://dx.doi.org/10.1016/s0040-4039(98)01221-0.

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40

Hong, Bor-Cherng, and Sheng-Fei Chin. "ChemInform Abstract: Bicyclo[3.2.1]octanes via McMurry Couplings." ChemInform 30, no. 47 (2010): no. http://dx.doi.org/10.1002/chin.199947108.

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41

Kraus, George A., Yung Son Hon, and James Sy. "Synthesis of bicyclo[3.2.1]octanes by ring contraction." Journal of Organic Chemistry 51, no. 14 (1986): 2625–27. http://dx.doi.org/10.1021/jo00364a001.

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42

Magedov, I. V., S. Yu Shapakin, V. N. Drozd, A. S. Batsanov, D. S. Yufit, and Yu T. Struchkov. "2,2,3,3-Tetracyano-7,8-dithiabicyclo[3.2.1]octanes: Structural studies." Chemistry of Heterocyclic Compounds 30, no. 6 (1994): 674–82. http://dx.doi.org/10.1007/bf01166308.

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43

Arbain, D., RD Wiryani, and MV Sargent. "A New Tropane Alkaloid From Pellacalyx axillaris." Australian Journal of Chemistry 44, no. 7 (1991): 1013. http://dx.doi.org/10.1071/ch9911013.

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Extraction of the fresh leaves and terminal branches of Pellacalyx axillaris Korth (Rhizophoraceae) yielded 8-azabicyclo[3.2.1]oct-endo-3-yl (E)-3-phenylprop-2-enoate (nortropinyl cinnamate) (1), the structure of which followed from its spectral properties and synthesis.

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44

Chen, Shuang-Wei, Cai-Hong Xu, Guo-Rong Zheng, and Xu-Hu Jin. "tert-Butyl 3-endo-3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate." Acta Crystallographica Section E Structure Reports Online 62, no. 4 (2006): o1233—o1234. http://dx.doi.org/10.1107/s1600536806006039.

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The title compound, C12H21NO3, is an important intermediate for new dopamine transporter inhibitors. The six-membered ring of the azabicyclo[3.2.1]octane system adopts a chair conformation with the hydroxyl group axial. The fused five-membered ring is in an envelope conformation.

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45

Meltzer, Peter C., Bing Wang, Zhengming Chen, et al. "Synthesis of 6- and 7- Hydroxy-8-azabicyclo[3.2.1]octanes and Their Binding Affinity for the Dopamine and Serotonin Transporters†." Journal of Medicinal Chemistry 44, no. 16 (2001): 2619–35. http://dx.doi.org/10.1021/jm0101242.

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46

Alizadeh, Abdolali, Vahideh Sadeghi, Fahimeh Bayat, and Long-Guan Zhu. "Highly Efficient Diastereoselective Synthesis of Azabicyclo[2.2.2]octanes." Synlett 25, no. 18 (2014): 2609–12. http://dx.doi.org/10.1055/s-0034-1379204.

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47

Miller, J. A., G. M. Ullah, G. M. Welsh, and A. C. Hall. "8-Aminobicyclo[3.2.1]octanes: synthesis and anti-viral activity." Tetrahedron Letters 42, no. 42 (2001): 7503–7. http://dx.doi.org/10.1016/s0040-4039(01)01593-3.

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48

Wachter, Michael P., Zoltan G. Hajos, Richard E. Adams, and Harvey M. Werblood. "Synthesis and interconversion of oxepanes and bicyclo[3.2.1]octanes." Journal of Organic Chemistry 50, no. 13 (1985): 2216–20. http://dx.doi.org/10.1021/jo00213a003.

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49

Ismiev, A. I., V. V. Dotsenko, N. A. Aksenov, G. Z. Mamedova, and A. M. Magerramov. "A New Synthetic Approach to Functionalized Bicyclo[3.2.1]octanes." Russian Journal of General Chemistry 88, no. 7 (2018): 1533–36. http://dx.doi.org/10.1134/s1070363218070289.

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50

Daude, Norbert, Ulrike Eggert, and H. M. R. Hoffmann. "A new synthesis of functionalized 6,8-dioxabicyclo[3.2.1]octanes." Journal of the Chemical Society, Chemical Communications, no. 3 (1988): 206. http://dx.doi.org/10.1039/c39880000206.

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