- Selective nickel-catalyzed dehydrogenative-decarboxylative formylation of indoles with glyoxylic acid
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Herein we present a new strategy for the dehydrogenative-decarboxylative coupling of indoles with glyoxylic acid. A broad range of indoles were transformed into the corresponding 3-formylindoles in moderate to good yields and excellent functional group tolerance. Notably, no N-formylation product was detected under our conditions.
- Yin, Zhiping,Wang, Zechao,Wu, Xiao-Feng
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- Cu-Catalyzed Dimerization of Indole Derived Oxime Acetate for Synthesis of Biimidazo[1,2- a]indoles
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A copper-mediated cyclization and dimerization of indole derived oxime acetate was developed to generate a series of biimidazo[1,2-a]indole scaffolds with two contiguous stereogenic quaternary carbons in one step.
- Xie, Tao,Sui, Qi-Bang,Qin, Lu-Zhe,Wen, Xiaoan,Sun, Hongbin,Xu, Qing-Long,Zhen, Le
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supporting information
p. 5518 - 5529
(2021/05/04)
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- Asymmetric Total Synthesis of Sarpagine and Koumine Alkaloids
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We report here a concise, collective, and asymmetric total synthesis of sarpagine alkaloids and biogenetically related koumine alkaloids, which structurally feature a rigid cage scaffold, with L-tryptophan as the starting material. Two key bridged skeleton-forming reactions, namely tandem sequential oxidative cyclopropanol ring-opening cyclization and ketone α-allenylation, ensure concurrent assembly of the caged sarpagine scaffold and installation of requisite derivative handles. With a common caged intermediate as the branch point, by taking advantage of ketone and allene groups therein, total synthesis of five sarpagine alkaloids (affinisine, normacusine B, trinervine, Na-methyl-16-epipericyclivine, and vellosimine) with various substituents and three koumine alkaloids (koumine, koumimine, and N-demethylkoumine) with more complex cage scaffolds has been accomplished.
- He, Ling,Jiang, Yan,Qiao, Zhen,Qiu, Hanyue,Su, Xiaojiao,Tan, Qiuyuan,Yang, Jiaojiao,Yang, Zhao,Zhang, Min,Zhou, Wenqiang
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supporting information
p. 13105 - 13111
(2021/05/10)
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- N-skatyltryptamines-dual 5-ht6r/d2r ligands with antipsychotic and procognitive potential
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A series of N-skatyltryptamines was synthesized and their affinities for serotonin and dopamine receptors were determined. Compounds exhibited activity toward 5-HT1A, 5-HT2A, 5-HT6, and D2 receptors. Substitution patterns resulting in affinity/activity switches were identified and studied using homology modeling. Chosen hits were screened to determine their metabolism, permeability, hepatotoxicity, and CYP inhibition. Several D2 receptor antagonists with additional 5-HT6R antagonist and agonist properties were identified. The former combination resembled known antipsychotic agents, while the latter was particularly interesting due to the fact that it has not been studied before. Selective 5-HT6R antagonists have been shown previously to produce procognitive and promnesic effects in several rodent models. Administration of 5-HT6R agonists was more ambiguous-in naive animals, it did not alter memory or produce slight amnesic effects, while in rodent models of memory impairment, they ameliorated the condition just like antagonists. Using the identified hit compounds 15 and 18, we tried to sort out the difference between ligands exhibiting the D2R antagonist function combined with 5-HT6R agonism, and mixed D2/5-HT6R antagonists in murine models of psychosis.
- Bojarski, Andrzej J.,Bugno, Ryszard,Cie?lik, Paulina,Duszyńska, Beata,Handzlik, Jadwiga,Hogendorf, Adam S.,Hogendorf, Agata,Kaczorowska, Katarzyna,Kurczab, Rafa?,Latacz, Gniewomir,Lenda, Tomasz,Sata?a, Grzegorz,Staroń, Jakub,Szewczyk, Bernadeta
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- Synthesis of polycyclic spirooxindoles via an asymmetric catalytic one-pot stepwise Aldol/chloroetherification/aromatization procedure
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A general method for the synthesis of chiral pentacyclic spirooxindoles containing a tetrahydropyrano[2,3-b]indole scaffold through a one-pot stepwise sequence from 3-(3-indolomethyl)oxindole, paraformaldehyde and NCS is reported. Furthermore, the pentacyclic spirooxindoles could be transformed to bispirooxindole and other structurally diverse spirocyclic oxindoles.
- Jiang, Yan,Yu, Shuo-Wen,Yang, Yi,Liu, Ying-Le,Xu, Xiao-Ying,Zhang, Xiao-Mei,Yuan, Wei-Cheng
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supporting information
p. 6647 - 6651
(2018/09/29)
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- Method for synthesizing indole -3 - formaldehyde compounds (by machine translation)
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The invention relates to a synthetic indole - 3 - formaldehyde compounds, which belongs to the technical field of organic synthesis. The invention will be indole compound, hexamethylene tetramine, crystalline aluminum trichloride, N, N - dimethyl formamide in proportion in 120 °C reaction under the condition of 1 - 20 the H, then filtered, washing, filtering, concentrating, column chromatography purification and other after-treatment technology, make the refined indole - 3 - formaldehyde compound. The invention overcomes the indole - 3 - benzaldehyde compound of preparation need to use not stabilized peroxide, and for a long time under the high temperature reaction of the defect. And the invention uses the advantages of simple equipment, product yield is high, the resulting yield of a target product can be up to 94%. In addition, the invention relates to a low reaction conditions, less catalyst levels, low energy consumption, the post treatment process is simple and easy to use, without the need of using a high dosage of acid or alkali, post-processing the solvent can be recovered and recycled, industrial "three wastes" is discharged little, suitable for large-scale production. (by machine translation)
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Paragraph 0041-0044; 0121-0124
(2018/08/28)
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- Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air
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An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.
- Wang, Qing-Dong,Zhou, Bin,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
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supporting information
p. 2670 - 2674
(2017/10/06)
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- Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air
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An efficient iodine-catalyzed chemoselective 3-formylation of free (N–H) and N-substituted indoles was achieved by using hexamethylenetetramine (HMTA) in the presence of activated carbon under air atmosphere. This new method could provide 3-formylindoles in moderate to excellent yields with fairly short reaction times. Moreover, this catalytic formylation of indoles procedure can be applied to gram-scale synthesis.
- Wang, Qing-Dong,Yang, Jin-Ming,Fang, Dong,Ren, Jiangmeng,Zeng, Bu-Bing
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supporting information
p. 2877 - 2880
(2017/07/11)
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- A 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drug (by machine translation)
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The invention belongs to the technical field of pharmaceutical chemistry, in particular to a kind of 1 - (phenyl) - 2, 3, 4, 9-tetrahydro -1H-pyrido [3,4-b] indole derivatives thereof in the preparation of the application of the anti-tumor drugs. Research display inhibit one or more prostandin receptor activity can be effective for the treatment of hypertension, at least one kind of prostagladin E2 receptor in the blood pressure regulating system RAAS in the course of play a crucial role, we by changing 1 and 8 is the angle of the two groups and the distance to EP3 receptor research, we developed a new high-efficiency of the synthetic route to study a series of derivatives, all of the target compound are all new product, all of the compound through the nuclear magnetic resonance and quality of the identification of the structure. The target compound in the antibacterial, anti-tumor, analgesic, anti-platelet aggregation, the promotion of kidney part of the reabsorption of sodium and water, regulating neurotransmitter release, promote adipose tissue Lipolysis and has an important role of anti-arrhythmia. (by machine translation)
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- Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides
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A highly efficient N,N′-dioxide-NiII catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98 % yield with up to 91 % enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). A promising approach: Catalytic de-aromatic [3+2] cycloaddition of indoles with epoxides by C-C cleavage of oxiranes is accomplished by using a highly efficient N,N′-dioxide-NiII catalyst system. A range of chiral furo[3,4-b]indoles is obtained with high enantiomeric excesses and diastereomeric ratios.
- Chen, Weiliang,Xia, Yong,Lin, Lili,Yuan, Xiao,Guo, Songsong,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 15104 - 15107
(2015/11/02)
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- Cu-mediated oxidative dimerization of skatole to tryptanthrin, an indolo[2,1-b]quinazolone alkaloid
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A one-pot conversion of skatole to tryptanthrin, an indolo[2,1-b]quinazoline alkaloid, was achieved by Cu-mediated oxidation.
- Itoh, Tomoki,Abe, Takumi,Nakamura, Shuhei,Ishikura, Minoru
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p. 1423 - 1428
(2015/07/15)
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- Diazonamide studies. A direct synthesis of the indole bis-oxazole fragment from tri- and tetra-peptides using biomimetic oxidative cyclizations
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The oxidation of several readily prepared tryptophan containing tri- and tetrapeptides with DDQ results in a biomimetic cyclization and direct formation of the indole bis-oxazole fragment of diazonamide A, establishing that such a transformation is a viab
- Sperry, Jonathan,Moody, Christopher J.
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experimental part
p. 6483 - 6495
(2010/10/19)
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- Synthesis of Macrocyclic Peptide Analogues of Proteasome Inhibitor TMC-95A
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The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(O)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.
- Berthelot, Alexandra,Piguel, Sandrine,Le Dour, Gwennael,Vidal, Joelle
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p. 9835 - 9838
(2007/10/03)
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- Synthetic studies towards the synthesis of western and eastern chloropeptin I, II subunits
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The western subunit (16-membered ring) was synthesized by the intramolecular SNAr reaction while the first 16-membered ring compound was obtained as a model of the eastern subunit via an intramolecular Ni0 mediated coupling reaction.
- Roussi, Georges,Gonzalez Zamora, Eduardo,Carbonnelle, Annie-Claude,Beugelmans, Rene
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p. 2041 - 2063
(2007/10/03)
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- A REGIOSELECTIVE AND COMMON SYNTHETIC METHOD OF DIHALOGENOINDOLES AND ITS APPLICATION FOR THE TOTAL SYNTHESES OF MARINE ALKALOIDS, 4,6-DIBROMO-, 4,6-DIBROMO-2-METHYL-, 3,4,5-TRIBROMOINDOLE
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A regioselective and common synthetic method for indoles carrying two different kinds of halogens was developed and applied successfully to the total syntheses of marine alkaloids, 4,6-dibromo- and 3,4,5-tribromoindole.The first total synthesis of 4,6-dibromo-2-methylindole is also reported.
- Ohta, Toshiharu,Yamato, Yoshinori,Tahira, Hiroko,Somei, Masanori
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p. 2817 - 2822
(2007/10/02)
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