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References (58)
-
Guy Lewin, C. Schaeffer, Catherine Dacquet (1997)
Perhydrogenation of tabersonine, ans Aspidiosperma indole alkaloid.Journal of natural products, 60 4
-
G. Singh, Z. Desta (2012)
Isatins as privileged molecules in design and synthesis of spiro-fused cyclic frameworks.Chemical reviews, 112 11
-
C. Yeung, V. Dong (2011)
Catalytic dehydrogenative cross-coupling: forming carbon-carbon bonds by oxidizing two carbon-hydrogen bonds.Chemical reviews, 111 3
-
T. Polossek, R. Ambros, S. Angerer, G. Brandl, A. Mannschreck, E. Angerer (1992)
6-Alkyl-12-formylindolo[2,1-a]isoquinolines. Syntheses, estrogen receptor binding affinities, and stereospecific cytostatic activity.Journal of medicinal chemistry, 35 19
-
P. Arockiam, C. Bruneau, P. Dixneuf (2012)
Ruthenium(II)-catalyzed C-H bond activation and functionalization.Chemical reviews, 112 11
-
R. Das, G. Kumar, M. Kapur (2017)
Amides as Weak Coordinating Groups in Proximal C–H Bond ActivationEuropean Journal of Organic Chemistry, 2017
-
Qiao Ren, Jiayao Huang, Lei Wang, Wenjun Li, H. Liu, Xuefeng Jiang, Jian Wang (2012)
Highly Efficient Assembly of 3-Hydroxy Oxindole Scaffold via a Catalytic Decarboxylative [1,2]-Addition StrategyACS Catalysis, 2
-
L. Ackermann, Lianhui Wang, R. Wolfram, A. Lygin (2012)
Ruthenium-catalyzed oxidative C-H alkenylations of anilides and benzamides in water.Organic letters, 14 3
-
Xiao Chen, K. Engle, Donghui Wang, Jin-Quan Yu (2009)
Palladium(II)‐katalysierte C‐H‐Aktivierung/C‐C‐Kreuzkupplung: Vielseitigkeit und AnwendbarkeitAngewandte Chemie, 121
-
Jin-Hyung Lee, Jintae Lee (2010)
Indole as an intercellular signal in microbial communities.FEMS microbiology reviews, 34 4
-
Maninder Kaur, Manjinder Singh, Navriti Chadha, O. Silakari (2016)
Oxindole: A chemical prism carrying plethora of therapeutic benefits.European journal of medicinal chemistry, 123
-
P. Nareddy, F. Jordan, M. Szostak (2017)
Recent Developments in Ruthenium-Catalyzed C–H Arylation: Array of Mechanistic ManifoldsACS Catalysis, 7
-
P. Magnus, T. Gallagher, J. BrownPeter, P. Pappalardo (1984)
The indole 2-3-quinodimethane strategy for the synthesis of indole alkaloidsAccounts of Chemical Research, 15
-
F. Patureau, F. Glorius (2010)
Rh catalyzed olefination and vinylation of unactivated acetanilides.Journal of the American Chemical Society, 132 29
-
Anna Kochanowska-Karamyan, M. Hamann (2010)
Marine indole alkaloids: potential new drug leads for the control of depression and anxiety.Chemical reviews, 110 8
-
R. Dalpozzo, G. Bartoli, Giorgio Bencivenni (2012)
Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones.Chemical Society reviews, 41 21
-
J. Powers, W. Meyer, Thomas Parsons (1967)
Protonation of the indole Grignard reagent and other organometallic derivatives of indoleJournal of the American Chemical Society, 89
-
D. Colby, R. Bergman, J. Ellman (2010)
Rhodium-catalyzed C-C bond formation via heteroatom-directed C-H bond activation.Chemical reviews, 110 2
-
Lanting Xu, Chao Zhang, Yu-Peng He, L. Tan, D. Ma (2016)
Rhodium-Catalyzed Regioselective C7-Functionalization of N-Pivaloylindoles.Angewandte Chemie, 55 1
-
Dong-Hui Wang, K. Engle, Bing‐Feng Shi, jin-quan yu (2010)
Ligand-Enabled Reactivity and Selectivity in a Synthetically Versatile Aryl C–H OlefinationScience, 327
-
K. Elumalai, W. Leong (2018)
Iridium-catalyzed carbonyl group-directed oxidative coupling of arenes with alkenesTetrahedron Letters, 59
-
Yuan Wei, Shigang Wen, Zu-Dong Liu, Xin‐Yan Wu, Bu-bing Zeng, Jinxing Ye (2015)
Diastereodivergent Catalytic Asymmetric Michael Addition of 2-Oxindoles to α,β-Unsaturated Ketones by Chiral Diamine Catalysts.Organic letters, 17 11
-
S. Sarkar, Weiping Liu, S. Kozhushkov, L. Ackermann (2014)
Weakly Coordinating Directing Groups for Ruthenium(II)‐ Catalyzed CH ActivationAdvanced Synthesis & Catalysis, 356
-
C. Swain, R. Baker, C. Kneen, J. Moseley, J. Saunders, E. Seward, G. Stevenson, M. Beer, J. Stanton, K. Watling (1991)
Novel 5-HT3 antagonists. Indole oxadiazoles.Journal of medicinal chemistry, 34 1
-
W. Gutekunst, P. Baran (2011)
C-H functionalization logic in total synthesis.Chemical Society reviews, 40 4
-
T. Gensch, M. Hopkinson, F. Glorius, J. Wencel‐Delord (2016)
Mild metal-catalyzed C-H activation: examples and concepts.Chemical Society reviews, 45 10
-
T. Nogrady, L. Morris (1966)
Indole hydrazides as potential monoamine oxidase inhibitors.Journal of medicinal chemistry, 9 3
-
Xi‐Sha Zhang, Kang Chen, Zhangjie Shi (2014)
Transition metal-catalyzed direct nucleophilic addition of C–H bonds to carbon–heteroatom double bondsChemical Science, 5
-
M. Reina, Wilfredo Ruiz-Mesía, M. López-Rodríguez, Lastenia Ruiz-Mesía, A. González-Coloma, R. Martínez-Díaz (2012)
Indole alkaloids from Geissospermum reticulatum.Journal of natural products, 75 5
-
C. Marti, E. Carreira (2003)
Construction of Spiro[pyrrolidine‐3,3′‐oxindoles] − Recent Applications to the Synthesis of Oxindole AlkaloidsEuropean Journal of Organic Chemistry, 2003
-
R. Dillard, N. Bach, S. Draheim, D. Berry, D. Carlson, N. Chirgadze, D. Clawson, L. Hartley, L. Johnson, N. Jones, E. Mckinney, E. Mihelich, J. Olkowski, R. Schevitz, A. Smith, D. Snyder, C. Sommers, J. Wery (1996)
Indole inhibitors of human nonpancreatic secretory phospholipase A2. 1. Indole-3-acetamides.Journal of medicinal chemistry, 39 26
-
P. Yates, Frederick MacLachlan, I. Rae, M. Rosenberger, A. Szabo, C. Willis, M. Cava, M. Behforouz, M. Lakshmikantham, W. Zeiger (1973)
Haplophytine. Novel type of indole alkaloidJournal of the American Chemical Society, 95
-
Arun Ghosh, G. Schiltz, R. Perali, S. Leshchenko, Stephanie Kay, D. Walters, Y. Koh, K. Maeda, H. Mitsuya (2006)
Design and synthesis of novel HIV-1 protease inhibitors incorporating oxyindoles as the P′2-ligandsBioorganic & Medicinal Chemistry Letters, 16
-
Veeranjaneyulu Lanke, K. Prabhu (2013)
Highly regioselective C2-alkenylation of indoles using the N-benzoyl directing group: an efficient Ru-catalyzed coupling reaction.Organic letters, 15 11
-
K. Williams, J. Kirkpatrick, B. Douglas, J. Weisbach (1969)
Synthesis of new indole alkaloid typesJournal of Organic Chemistry, 34
-
M. Goldbrunner, G. Loidl, T. Polossek, A. Mannschreck, E. Angerer (1997)
Inhibition of tubulin polymerization by 5,6-dihydroindolo[2,1-alpha]isoquinoline derivatives.Journal of medicinal chemistry, 40 22
-
P. Gore, G. Hughes, E. Ritchie (1949)
The Fischer Indole SynthesisNature, 164
-
J. Wencel‐Delord, T. Dröge, Fan Liu, F. Glorius (2011)
Towards mild metal-catalyzed C-H bond activation.Chemical Society reviews, 40 9
-
B. Hachuła, M. Zubko, P. Zajdel, M. Książek, J. Kusz, Oliwia Starczewska, J. Janek, W. Pisarski (2018)
Polymorphs of oxindole as the core structures in bioactive compoundsCrystEngComm, 20
-
Xiao Chen, K. Engle, Dong-Hui Wang, jin-quan yu (2009)
Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.Angewandte Chemie, 48 28
-
Nils Schröder, T. Besset, F. Glorius (2012)
Synthesis of Olefin-Oxazoline Ligands (OlefOx) by Rhodium(III)-Catalyzed Oxidative OlefinationAdvanced Synthesis & Catalysis, 354
-
K. Shen, Xiaohua Liu, Lili Lin, Xiaoming Feng (2012)
Recent progress in enantioselective synthesis of C3-functionalized oxindoles: rare earth metals take actionChemical Science, 3
-
Yulong Sun, Jia Liu, Xianxing Jiang, Tao Sun, Luping Liu, Xiao-yuan Zhang, Shaoli Ding, Jing-yi Li, Y. Zhuang, Yiqing Wang, Rui Wang (2015)
One-Step Synthesis of Chiral Oxindole-type Analogues with Potent Anti-inflammatory and Analgesic ActivitiesScientific Reports, 5
-
Jean Bras, J. Muzart (2011)
Intermolecular dehydrogenative Heck reactions.Chemical reviews, 111 3
-
K. Lackey, M. Cory, Ronda Davis, S. Frye, P. Harris, R. Hunter, D. Jung, O. McDonald, R. Mcnutt, M. Peel, R. Rutkowske, J. Veal, E. Wood (2000)
The discovery of potent cRaf1 kinase inhibitors.Bioorganic & medicinal chemistry letters, 10 3
-
Mei–Fen Bao, Chun-Xia Zeng, Ya-Ping Liu, Bing-Jie Zhang, Ling Ni, Xiao-Dong Luo, Xiang-Hai Cai (2017)
Indole Alkaloids from Hunteria zeylanica.Journal of natural products, 80 4
-
A. Gupta, M. Bharadwaj, Anoop Kumar, R. Mehrotra (2017)
Spiro-oxindoles as a Promising Class of Small Molecule Inhibitors of p53–MDM2 Interaction Useful in Targeted Cancer TherapyTopics in Current Chemistry, 375
-
S. Edmondson, S. Danishefsky, L. Sepp-Lorenzino, N. Rosen (1999)
Total Synthesis of Spirotryprostatin A, Leading to the Discovery of Some Biologically Promising AnaloguesJournal of the American Chemical Society, 121
-
Carlo Sambiagio, David Schönbauer, R. Blieck, Toan Dao-Huy, G. Pototschnig, P. Schaaf, T. Wiesinger, M. Zia, J. Wencel‐Delord, T. Besset, B. Maes, M. Schnürch (2018)
A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistryChemical Society Reviews, 47
-
I. Beletskaya, A. Cheprakov (2000)
The heck reaction as a sharpening stone of palladium catalysis.Chemical reviews, 100 8
-
R. Ambros, Martin Schneider, S. Angerer (1990)
Indolo[2,1-a]isoquinolines. Syntheses, steroid hormone receptor binding affinities, and cytostatic activity.Journal of medicinal chemistry, 33 1
-
M. Boele, G. Strijdonck, André Vries, P. Kamer, J. Vries, P. Leeuwen (2002)
Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature.Journal of the American Chemical Society, 124 8
-
S. Rakshit, Christoph Grohmann, T. Besset, F. Glorius (2011)
Rh(III)-catalyzed directed C-H olefination using an oxidizing directing group: mild, efficient, and versatile.Journal of the American Chemical Society, 133 8
-
K. Higuchi, T. Kawasaki (2005)
Simple indole alkaloids and those with a nonrearranged monoterpenoid unit.Natural product reports, 24 4
-
F. Zhou, Yun‐Lin Liu, Jian Zhou (2010)
Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 PositionAdvanced Synthesis & Catalysis, 352
-
T. Besset, N. Kuhl, F. Patureau, F. Glorius (2011)
Rh(III)-catalyzed oxidative olefination of vinylic C-H bonds: efficient and selective access to di-unsaturated α-amino acid derivatives and other linear 1,3-butadienes.Chemistry, 17 26
-
Chengguo Jia, T. Kitamura, Y. Fujiwara (2001)
Catalytic functionalization of arenes and alkanes via C-H bond activation.Accounts of chemical research, 34 8
-
G. Song, Fen Wang, Xingwei Li (2012)
C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation.Chemical Society reviews, 41 9
- Publisher
- Wiley
- Copyright
- © 2018 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
- ISSN
- 2193-5807
- eISSN
- 2193-5815
- DOI
- 10.1002/ajoc.201800605
- Publisher site
- See Article on Publisher Site
Abstract
Rhodium(III)‐catalyzed oxindole‐directed oxidative Heck‐type olefination reactions of N‐aryloxindoles and olefins represent an efficient approach for the construction of C−C bond. It offers a straightforward and atom‐economical method for the synthesis of functionalized oxindole alkenylation derivatives in moderate to excellent yields.
Journal
Asian Journal of Organic Chemistry – Wiley
Published: Dec 1, 2018
Keywords: ; ; ; ;