- A mild Bischler–Napieralski-type cyclization of trichloromethyl carbamates for the synthesis of β -carbolinones
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– A straightforward synthesis of β-carbolinones by the Bischler–Napieralski-type cyclization of the corresponding trichloromethyl carbamates, which does not require acids, bases, oxidants, or transition-metals to promote the cyclization, has been achieved.
- Hirao, Seiya,Kitamori, Mayumi,Itoh, Tomoki,Chiba, Yuusuke,Abe, Takumi
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p. 235 - 250
(2020/02/11)
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- Site-Selective Carbonylative Synthesis of Structurally Diverse Lactams from Heterocyclic Amines with TFBen as the CO Source
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A palladium-catalyzed site-selective C-H carbonylation of heterocyclic amines for the synthesis of lactam motifs has been developed. The reaction of 3-thiophene methylamines, 2-thiophene methylamines, and tryptamines with benzene-1,3,5-triyl triformate (TFBen) as the CO source provides a series of structurally diverse lactams in moderate to high yields with excellent regioselectivities.
- Ying, Jun,Gao, Qian,Wu, Xiao-Feng
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p. 14297 - 14305
(2019/11/03)
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- Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones
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The Pd/Cu cocatalyzed oxidative tandem C-H aminocarbonylation and dehydrogenation was developed, affording carbolinones with molecular oxygen as the terminal oxidant. Natural product strychnocarpine and its derivatives were prepared conveniently using this strategy.
- Han, Hui,Xia, Ji-Bao,Yang, Shang-Dong
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p. 3357 - 3369
(2019/04/06)
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- PIDA/I2-Mediated α- And β-C(sp3)-H Bond Dual Functionalization of Tertiary Amines
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The α,β-C(sp3)-H bond dual functionalization of tertiary amines is still a challenging task for both organic and medicinal chemists. Herein a direct, mild, metal-free, and site-specific method mediated by PIDA/I2 was developed for α,
- Zhu, Yu,Shao, Li-Dong,Deng, Zhen-Tao,Bao, Ying,Shi, Xin,Zhao, Qin-Shi
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p. 10166 - 10174
(2018/08/01)
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- Method for synthesizing tetrahydro beta-carboline-1-one compound through palladium catalysis
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The invention discloses a method for synthesizing a tetrahydro beta-carboline-1-one compound through palladium catalysis. According to the method, carbonic oxide is used as a carbonyl source; the carbonic oxide and a tryptamine type compound react at ordinary pressure for efficiently preparing the tetrahydro beta-carboline-1-one compound. The method has the advantages that the tetrahydro beta-carboline-1-one compound with great application prospects is effectively prepared by using the carbonic oxide at the ordinary pressure as the carbonyl source and using bivalent metal palladium as a catalyst. From the angle of production and economy, through being compared with high-pressure reaction, the method has the advantages that the reaction cost is greatly reduced through carbonic oxide gas at normal temperature, and the reaction operability is improved.
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Paragraph 0034; 0035; 0036
(2017/10/06)
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- Design, synthesis, and biological evaluation of novel (1-thioxo-1,2,3,4- tetrahydro-β-carbolin-9-yl)acetic acids as selective inhibitors for AKR1B1
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New substituted (1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acids were designed as the inhibitor of AKR1B1 based upon the structure of rhetsinine, a minor alkaloidal component of Evodia rutaecarpa, and twenty derivatives were synthesized and evaluated. The most active compound of the series was (2-benzyl-6-methoxy-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl) acetic acid (7m), which showed comparable inhibitory activity for AKR1B1 (IC50 = 0.15 μM) with clinically used epalrestat (IC50 = 0.1 μM). In the view of activity and selectivity, the most potent compound was (2-benzyl-6-carboxy-1-thioxo-1,2,3,4-tetrahydro-β-carbolin-9-yl)acetic acid (7t), which showed strong inhibitory effect (IC50 = 0.17 μM) and very high selectivity for AKR1B1 against AKR1A1 (311:1) and AKR1B10 (253:1) compared with epalrestat.
- Minehira, Daisuke,Takeda, Daisuke,Urata, Hirokazu,Kato, Atsushi,Adachi, Isao,Wang, Xu,Matsuya, Yuji,Sugimoto, Kenji,Takemura, Mayuko,Endo, Satoshi,Matsunaga, Toshiyuki,Hara, Akira,Koseki, Jun,Narukawa, Kayo,Hirono, Shuichi,Toyooka, Naoki
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scheme or table
p. 356 - 367
(2012/03/09)
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- An autoxidative approach to 1,2,3,4-tetrahydroisoquinolin-1-one and tetrahydro-β-carbolin-1-one
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Treatment of N-benzyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylate with sodium hydride in N,N-dimethylformamide gives the corresponding N-benzyl 1,2,3,4-tetrahydroisoquinolin-1-one in quantitative yield. The N-benzyl 1,2,3,4-tetrahydro-β-carbolin-1-one is prepared in a similar fashion. The N-deprotection occurred concomitantly with the oxidative decarboxylation when the nitrogen was benzyloxycarbonylated.
- Bois-Choussy, Michèle,De Paolis, Micha?l,Zhu, Jieping
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p. 3427 - 3430
(2007/10/03)
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- Synthesis and Serotonin-Receptor Activity of Substituted 1-Oxo-1,2,3,4-tetrahydro-&β-carbolines
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2,3-Dihydroxypyridine is used as a starting material for the synthesis of donor and acceptor substituted 1-oxo-1,2,3,4-tetrahydro-β-carbolines via Fisher indole cyclisation.An alkaloid from Alstonia venenata is prepared.All compounds inclusive strychnocarpine show low affinity to the serotonine receptor. - Key words: 3-Hydroxy-2-pyridone, Strychnocarpine Derivatives, 5-Hydroxytryptamine Receptor Stimulators
- Herdeis, Claus,Bissinger, Gerhard
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p. 785 - 790
(2007/10/02)
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