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Journal articles on the topic 'Azabicycles'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Kadikova, Gulnara N., Vladimir A. D’yakonov та Usein M. Dzhemilev. "Synthesis of New Functionally Substituted 9-Azabicyclo[4.2.1]nona-2,4,7-trienes by Cobalt(I)-Catalyzed [6π + 2π]-Cycloaddition of N-Carbocholesteroxyazepine to Alkynes". Molecules 26, № 10 (2021): 2932. http://dx.doi.org/10.3390/molecules26102932.

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Catalytic [6π + 2π]-cycloaddition of N-carbocholesteroxyazepine with functionally substituted terminal alkynes and 1,4-butynediol was performed for the first time under the action of the Co(acac)2(dppe)/Zn/ZnI2 three-component catalytic system. The reaction gave previously undescribed but promising 9-azabicyclo[4.2.1]nona-2,4,7-trienes (in 79–95% yields), covalently bound to a natural metabolite, cholesterol. The structure of the synthesized azabicycles was confirmed by analysis of one- and two-dimensional (1H, 13C, DEPT 13C, COSY, NOESY, HSQC, HMBC) NMR spectra.

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2

Krow, Grant R., Fang Yu, Matthew Sender, et al. "Introduction of C(5/6) side chains onto 2-azabicyclo[2.1.1]hexanes via a 6-anti-bromo-5-anti-hydroxy derivative." Canadian Journal of Chemistry 90, no. 1 (2012): 121–30. http://dx.doi.org/10.1139/v11-112.

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Oxidation of the title bromoalcohol provided the strained ketone, 5-bromo-6-oxo-2-azabicyclo[2.1.1]hexane. Additions of nucleophiles to either this or the debrominated ketone have been used to introduce 5(6)-syn-alkyl and aryl groups, 5(6)-alkylidene linkages, and 5(6)-anti-alkyl and acyl substituents. Facial selectivity is for additions to the 6-bromo-5-ketone and 5-alkylidene azabicycles to occur from the face syn to the nitrogen atom. The bromine atom of the title alcohol has also been replaced by a 6-anti-(1-hydroxyethyl) substituent using a directed radical addition process. The stereosel

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3

Alanine, T. A., W. R. J. D. Galloway, S. Bartlett, J. J. Ciardiello, T. M. McGuire, and D. R. Spring. "Concise synthesis of rare pyrido[1,2-a]pyrimidin-2-ones and related nitrogen-rich bicyclic scaffolds with a ring-junction nitrogen." Organic & Biomolecular Chemistry 14, no. 3 (2016): 1031–38. http://dx.doi.org/10.1039/c5ob01784j.

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4

Disadee, Wannaporn, and Somsak Ruchirawat. "One-pot cascade synthesis of azabicycles via the nitro-Mannich reaction and N-alkylation." Organic & Biomolecular Chemistry 16, no. 5 (2018): 707–11. http://dx.doi.org/10.1039/c7ob03104a.

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5

Choi, Chulho, Philippe Nuhant, James J. Mousseau, et al. "Synthesis of Chiral Azabicycles from Pyroglutaminols." Organic Letters 18, no. 21 (2016): 5748–51. http://dx.doi.org/10.1021/acs.orglett.6b03024.

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6

Belostotskii, Anatoly M., and Elena Markevich. "Conformational Dynamics in Nitrogen-Fused Azabicycles." Journal of Organic Chemistry 68, no. 8 (2003): 3055–63. http://dx.doi.org/10.1021/jo0266691.

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7

Greenaway, Rebecca L., Craig D. Campbell, Oliver T. Holton, C. Adam Russell, and Edward A. Anderson. "Palladium-Catalyzed Cascade Cyclization of Ynamides to Azabicycles." Chemistry - A European Journal 17, no. 51 (2011): 14366–70. http://dx.doi.org/10.1002/chem.201102880.

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8

Martínez-Estíbalez, Unai, Nuria Sotomayor, and Esther Lete. "Pd-catalyzed arylation/ring-closing metathesis approach to azabicycles." Tetrahedron Letters 48, no. 16 (2007): 2919–22. http://dx.doi.org/10.1016/j.tetlet.2007.02.070.

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9

Reggelin, Michael, Jochen Kühl, Jan Kaiser, and Philipp Bühle. "Synthesis of Highly Functionalized Azabicycles via 2-Alkenyl Sulfoximines." Synthesis 2006, no. 13 (2006): 2224–32. http://dx.doi.org/10.1055/s-2006-942427.

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10

Belkacemi, Djballah, John W. Davies, John R. Malpass, Antoinette Naylor (née Bathgate), and Craig R. Smith. "15N nuclear magnetic resonance studies of azabicycles; unusual deshielding of nitrogen in the 7-azabicyclo[2.2.1]heptyl ring system." Tetrahedron 48, no. 46 (1992): 10161–76. http://dx.doi.org/10.1016/s0040-4020(01)89045-1.

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11

BELKACEMI, D., J. W. DAVIES, J. R. MALPASS, A. NAYLOR, and C. R. SMITH. "ChemInform Abstract: 15N NMR Studies of Azabicycles; Unusual Deshielding of Nitrogen in the 7-Azabicyclo(2.2.1)heptyl Ring System." ChemInform 24, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199311057.

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12

Rizzo, Antonio, and Syuzanna R. Harutyunyan. "Azabicycles construction: the transannular ring contraction with N-protected nucleophiles." Org. Biomol. Chem. 12, no. 34 (2014): 6570–79. http://dx.doi.org/10.1039/c4ob01311e.

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13

Greenaway, Rebecca L., Craig D. Campbell, Oliver T. Holton, C. Adam Russell, and Edward A. Anderson. "ChemInform Abstract: Palladium-Catalyzed Cascade Cyclization of Ynamides to Azabicycles." ChemInform 43, no. 20 (2012): no. http://dx.doi.org/10.1002/chin.201220106.

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14

Stockman, Robert A., Peter Szeto, Stephen H. J. Thompson, Michael S. Hadley, David C. Lathbury, and Timothy Gallagher. "Synthesis of Functionalised Azabicycles via a Regiospecific Intramolecular Aldol Reaction." Synlett 1996, no. 09 (1996): 853–55. http://dx.doi.org/10.1055/s-1996-5598.

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15

Rizzo, Antonio, and Syuzanna R. Harutyunyan. "ChemInform Abstract: Azabicycles Construction: The Transannular Ring Contraction with N-Protected Nucleophiles." ChemInform 45, no. 40 (2014): no. http://dx.doi.org/10.1002/chin.201440254.

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16

STOCKMAN, R. A., P. SZETO, S. H. J. THOMPSON, M. S. HADLEY, D. C. LATHBURY, and T. GALLAGHER. "ChemInform Abstract: Synthesis of Functionalized Azabicycles via a Regiospecific Intramolecular Aldol Reaction." ChemInform 28, no. 8 (2010): no. http://dx.doi.org/10.1002/chin.199708121.

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17

Li, Mingming, Ping Xing, and Biao Jiang. "A novel and efficient route to azabicycles via the isocyanate-mediated twofold cyclization." Tetrahedron 72, no. 11 (2016): 1455–60. http://dx.doi.org/10.1016/j.tet.2016.01.050.

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18

Evans, P. Andrew, Thara Manangan, and Arnold L. Rheingold. "Stereoselective Construction oftrans-Disubstituted Azabicycles Using Oxauracil as a Novel Free Radical Acceptor." Journal of the American Chemical Society 122, no. 44 (2000): 11009–10. http://dx.doi.org/10.1021/ja0020308.

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19

Sonar, Vijayakumar N., Sean Parkin, and Peter A. Crooks. "(Z)-2-(3-Hydroxy-4-methoxybenzylidene)-1-azabicyclo[2.2.2]octan-3-one." Acta Crystallographica Section C Crystal Structure Communications 59, no. 11 (2003): o647—o649. http://dx.doi.org/10.1107/s0108270103022339.

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Crystals of the title compound, C15H17NO3, were obtained from a condensation reaction of 3-hydroxy-4-methoxybenzaldehyde with 1-azabicyclo[2.2.2]octan-3-one and subsequent crystallization of the product from methanol. The title compound, containing a double bond that connects the azabicyclic ring system to the 3-hydroxy-4-methoxybenzylidene group, was obtained with Z geometry.

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20

Chio, Freda K. I., Sébastien J. J. Guesné, Lorraine Hassall, Thomas McGuire, and Adrian P. Dobbs. "Synthesis of Azabicycles via Cascade Aza-Prins Reactions: Accessing the Indolizidine and Quinolizidine Cores." Journal of Organic Chemistry 80, no. 20 (2015): 9868–80. http://dx.doi.org/10.1021/acs.joc.5b01301.

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21

Oliveira, Mona, Lourenço Luis Botelho de Santana, José Claudio Serafim, et al. "Design, synthesis and cytotoxicity of the antitumor agent 1-azabicycles for chemoresistant glioblastoma cells." Investigational New Drugs 38, no. 5 (2019): 1257–71. http://dx.doi.org/10.1007/s10637-019-00877-2.

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22

Choi, Kyung Il, Joo Hwan Cha, Yong Seo Cho, et al. "Binding affinities of 3-(3-phenylisoxazol-5-yl)methylidene-1-azabicycles to acetylcholine receptors." Bioorganic & Medicinal Chemistry Letters 9, no. 19 (1999): 2795–800. http://dx.doi.org/10.1016/s0960-894x(99)00477-1.

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23

Stockman, Robert, Pooja Aggarwal, George Procopiou, Diane Robbins, Gareth Harbottle, and William Lewis. "Combining Two-Directional Synthesis and Tandem Reactions, Part 17: Expedient Formation of Functionalised Azabicycles." Synlett 23, no. 03 (2012): 423–27. http://dx.doi.org/10.1055/s-0031-1290138.

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24

Kuznetsov, N. Yu, K. A. Lyssenko, A. S. Peregudov, and Yu N. Bubnov. "Synthesis of bridged azabicycles from isoquinolines via a tandem of allylboration and intramolecular metathesis." Russian Chemical Bulletin 56, no. 8 (2007): 1569–74. http://dx.doi.org/10.1007/s11172-007-0245-3.

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25

Kuznetsov, Nikolai Yu, Viktor N. Khrustalev, Ivan A. Godovikov, and Yuri N. Bubnov. "Synthesis of Bridged Azabicycles from Pyridines and Pyrrole by a Diallylboration - Ring Closing Metathesis Sequence." European Journal of Organic Chemistry 2006, no. 1 (2006): 113–20. http://dx.doi.org/10.1002/ejoc.200500560.

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26

Yeh, Ming-Chang P., Chia-Jung Liang, Tzu-Lin Huang, Hsiao-Ju Hsu, and Yu-Shuo Tsau. "Transition-Metal-Free Carbofluorination of TBS-Protected Nitrogen-Containing Cyclic Enynols: Synthesis of Fluorinated Azabicycles." Journal of Organic Chemistry 78, no. 11 (2013): 5521–29. http://dx.doi.org/10.1021/jo400634c.

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27

Prakash, Praveen, E. Jijy, P. S. Aparna, S. Viji, and K. V. Radhakrishnan. "Rhodium(III) catalyzed synthesis of isoquinolone fused azabicycles through C–H activation of N-pivaloyloxy benzamides." Tetrahedron Letters 55, no. 4 (2014): 916–20. http://dx.doi.org/10.1016/j.tetlet.2013.12.049.

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28

Archambeau, Alexis, and Tomislav Rovis. "Rhodium(III)‐Catalyzed Allylic C(sp 3 )–H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles." Angewandte Chemie 127, no. 45 (2015): 13535–38. http://dx.doi.org/10.1002/ange.201504150.

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29

Evans, P. Andrew, Thara Manangan, and Arnold L. Rheingold. "ChemInform Abstract: Stereoselective Construction of trans-Disubstituted Azabicycles Using Oxauracil as a Novel Free Radical Acceptor." ChemInform 32, no. 13 (2001): no. http://dx.doi.org/10.1002/chin.200113153.

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30

Aggarwal, Pooja, George Procopiou, Diane Robbins, Gareth Harbottle, William Lewis, and Robert A. Stockman. "ChemInform Abstract: Combining Two-Directional Synthesis and Tandem Reactions. Part 17. Expedient Formation of Functionalized Azabicycles." ChemInform 43, no. 23 (2012): no. http://dx.doi.org/10.1002/chin.201223157.

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31

Chio, Freda K. I., Sebastien J. J. Guesne, Lorraine Hassall, Thomas McGuire, and Adrian P. Dobbs. "ChemInform Abstract: Synthesis of Azabicycles via Cascade Aza-Prins Reactions: Accessing the Indolizidine and Quinolizidine Cores." ChemInform 47, no. 9 (2016): no. http://dx.doi.org/10.1002/chin.201609037.

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32

Archambeau, Alexis, and Tomislav Rovis. "Rhodium(III)‐Catalyzed Allylic C(sp 3 )–H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles." Angewandte Chemie International Edition 54, no. 45 (2015): 13337–40. http://dx.doi.org/10.1002/anie.201504150.

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33

Parthiban, Paramasivam, Paramasivam Rathika, Venkatachalam Ramkumar, Se Mo Son, and Yeon Tae Jeong. "Stereospecific synthesis of oximes and oxime ethers of 3-azabicycles: A SAR study towards antimicrobial agents." Bioorganic & Medicinal Chemistry Letters 20, no. 5 (2010): 1642–47. http://dx.doi.org/10.1016/j.bmcl.2010.01.048.

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34

An, Qianjin, Delong Liu, Jiefeng Shen, Yangang Liu, and Wanbin Zhang. "The Construction of Chiral Fused Azabicycles Using a Pd-Catalyzed Allylic Substitution Cascade and Asymmetric Desymmetrization Strategy." Organic Letters 19, no. 1 (2016): 238–41. http://dx.doi.org/10.1021/acs.orglett.6b03529.

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35

Kuznetsov, N. Yu, and Yu N. Bubnov. "Ruthenium-catalyzed intramolecular metathesis of dienes and its application in the synthesis of bridged and spiro azabicycles." Russian Chemical Reviews 84, no. 7 (2015): 758–85. http://dx.doi.org/10.1070/rcr4478.

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36

Archambeau, Alexis, and Tomislav Rovis. "ChemInform Abstract: Rhodium(III)-Catalyzed Allylic C(sp3)-H Activation of Alkenyl Sulfonamides: Unexpected Formation of Azabicycles." ChemInform 47, no. 10 (2016): no. http://dx.doi.org/10.1002/chin.201610127.

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37

Yeh, Ming-Chang P., Chia-Jung Liang, Tzu-Lin Huang, Hsiao-Ju Hsu, and Yu-Shuo Tsau. "ChemInform Abstract: Transition-Metal-Free Carbofluorination of TBS-Protected Nitrogen-Containing Cyclic Enynols: Synthesis of Fluorinated Azabicycles." ChemInform 44, no. 40 (2013): no. http://dx.doi.org/10.1002/chin.201340165.

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38

John, Jubi, Rani Rajan, S. Sarath Chand, et al. "Palladium catalyzed reaction of ortho-functionalized aryl iodides with bicyclic hydrazines: facile route toward heteroannulated cyclopentenes and azabicycles." Tetrahedron 69, no. 1 (2013): 152–59. http://dx.doi.org/10.1016/j.tet.2012.10.053.

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39

Prakash, Praveen, E. Jijy, P. S. Aparna, S. Viji, and K. V. Radhakrishnan. "ChemInform Abstract: Rhodium(III) Catalyzed Synthesis of Isoquinolone Fused Azabicycles Through C-H Activation of N-Pivaloyloxy Benzamides." ChemInform 45, no. 27 (2014): no. http://dx.doi.org/10.1002/chin.201427175.

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40

Zeng, Ziyu, Gabriele Kociok-Köhn, Timothy J. Woodman, Michael G. Rowan, and Ian S. Blagbrough. "The 1H NMR Spectroscopic Effect of Steric Compression Is Found in [3.3.1]Oxa- and Azabicycles and Their Analogues." ACS Omega 6, no. 19 (2021): 12769–86. http://dx.doi.org/10.1021/acsomega.1c01093.

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41

Olesen, PH, P. Sauerberg, S. Treppendahl, et al. "3-(3-Alkylthio-1,2,5-thiadiazol-4-yl)-1-azabicycles. Structure—activity relationships for antinociception mediated by central muscarinic receptors." European Journal of Medicinal Chemistry 31, no. 3 (1996): 221–30. http://dx.doi.org/10.1016/0223-5234(96)89138-0.

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42

Cunha, Silvio, Raimundo Francisco dos Santos Filho, Katharine Hodel Saraiva, Alene Vanessa Azevedo-Santos, and Diego Menezes. "Synthesis of multi-functionalized 1-azabicycles through MAOS acid catalyzed formal aza-[3+3] cycloaddition of heterocyclic enaminones with oxazolones." Tetrahedron Letters 54, no. 26 (2013): 3366–70. http://dx.doi.org/10.1016/j.tetlet.2013.04.055.

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43

Klaver, Wim J., Henk Hiemstra, and W. Nico Speckamp. "Diastereoselective alkylation of the dianion of 5-ethoxy-4(S)-hydroxy-1-isopropyl-2-pyrrolidinone; Synthesis of enantiomerically pure azabicycles." Tetrahedron Letters 28, no. 14 (1987): 1581–84. http://dx.doi.org/10.1016/s0040-4039(01)81047-9.

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44

Evans, P. Andrew, Thara Manangan, and Arnold L. Rheingold. "Stereoselective Construction oftrans-Disubstituted Azabicycles Using Oxauracil as a Novel Free Radical Acceptor [J. Am. Chem. Soc.2000,122, 11009−11010]." Journal of the American Chemical Society 127, no. 47 (2005): 16745. http://dx.doi.org/10.1021/ja056443q.

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45

Shi, Shicheng, and Michal Szostak. "Aminoketyl Radicals in Organic Synthesis: Stereoselective Cyclization of Five- and Six-Membered Cyclic Imides to 2-Azabicycles Using SmI2–H2O." Organic Letters 17, no. 20 (2015): 5144–47. http://dx.doi.org/10.1021/acs.orglett.5b02732.

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46

John, Jubi, Rani Rajan, S. Sarath Chand, et al. "ChemInform Abstract: Palladium Catalyzed Reaction of ortho-Functionalized Aryl Iodides with Bicyclic Hydrazines: Facile Route Toward Heteroannulated Cyclopentenes and Azabicycles." ChemInform 44, no. 25 (2013): no. http://dx.doi.org/10.1002/chin.201325047.

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47

OLESEN, P. H., P. SAUERBERG, S. TREPPENDAHL, et al. "ChemInform Abstract: 3-(3-Alkylthio-1,2,5-thiadiazol-4-yl)-1-azabicycles. Structure- Activity Relationships for Antinociception Mediated by Central Muscarinic Receptors." ChemInform 27, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199627171.

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48

Cortez, G. Alex, Carl A. Baxter, Richard R. Schrock, and Amir H. Hoveyda. "Comparison of Ru- and Mo-Based Chiral Olefin Metathesis Catalysts. Complementarity in Asymmetric Ring-Opening/Cross-Metathesis Reactions of Oxa- and Azabicycles." Organic Letters 9, no. 15 (2007): 2871–74. http://dx.doi.org/10.1021/ol071008h.

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49

Szostak, Michal, Shicheng Shi, and Roger Lalancette. "Cyclization of Imides to 2-Azabicycles via Aminoketyl Radicals by Using Samarium(II) Iodide–Water: Reaction Development, Synthetic Scope, and Mechanistic Studies." Synthesis 48, no. 12 (2016): 1825–54. http://dx.doi.org/10.1055/s-0035-1560437.

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50

Bock, Christina M., Gangajji Parameshwarappa, Simon Bönisch, et al. "Generation of Complex Azabicycles and Carbobicycles from Two Simple Compounds in a Single Operation through a Metal-Free Six-Step Domino Reaction." Chemistry - A European Journal 22, no. 15 (2016): 5189–97. http://dx.doi.org/10.1002/chem.201504798.

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