- Replacing halogenated solvents by a butyl acetate solution of bisphenol S in the transformations of indoles
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A butyl acetate solution of bisphenol S (BPS) was proved to be able to replace hazardous halogenated solvents in the transformation of indoles. Measurement with Kamlet-Taft solvatochromic parameters disclosed that the polarity of the BPS-containing butyl acetate was enhanced greatly. The protocol not only conferred a convenient way to minimize the use of halogenated solvents in the synthesis of indole derivatives, but also enabled successful recycling of both the butyl acetate solvent and BPS additive, strengthening the greenness of the reaction systems.
- Bai, Rongxian,Ferlin, Francesco,Gao, Feng,Gu, Yanlong,Li, Minghao,Vaccaro, Luigi
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supporting information
p. 3588 - 3594
(2021/06/06)
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- Copper-Catalyzed Synthesis of Indolyl Benzo[b]carbazoles and Their Photoluminescence Property
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A copper-catalyzed cascade cyclization of dihydroisobenzofurans with indoles for the rapid construction of indoly benzo[b]carbazoles has been reported, providing the desired products in moderate to good yields under mild conditions along with a broad substrate scope and good functional group tolerance. The photoluminescence property of these indoly benzo[b]carbazoles has also been investigated.
- Hao, Tonggang,Huang, Long,Wei, Yin,Shi, Min
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supporting information
p. 5133 - 5137
(2021/07/19)
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- Method for methylation reaction
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The invention relates to a method for a methylation reaction. The method is characterized in that a reaction substrate is reacted in an organic solvent in the presence of an alkali with methyl trifluoroacetate as a methylation reagent to obtain a corresponding methylated product. The method is a new methylation method, and has the advantages of cheapness, easiness in operation, mild reaction conditions, wide application range of the substrate, avoiding of dimethyl sulfate, iodomethane and other highly toxic methylation reagents, and obtaining of the methylated product with a high yield.
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Paragraph 0013
(2019/01/21)
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- Photocatalytic Alkylation of Pyrroles and Indoles with α-Diazo Esters
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This article describes the photoalkylation of electron-rich aromatic compounds with diazo esters. C-2-alkylated indoles and pyrroles are obtained with good yields even though the photocatalyst loading is as low as 0.075 mol %. For EWG-substituted substrates, the addition of a catalytic amount of N,N-dimethyl-4-methoxyaniline is required. Both EWG-EWG- and EWG-EDG-substituted diazo esters are suitable as alkylating agents. The reaction selectivity and mechanistic experiments suggest that carbenes/carbenoid intermediates are not involved in the reaction pathway.
- Ciszewski, Lukasz W.,Durka, Jakub,Gryko, Dorota
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supporting information
p. 7028 - 7032
(2019/09/12)
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- Tandem Rh(III)-Catalyzed C-H Heteroarylation of Indolyl Ketones and Cu(II)-Promoted Intramolecular Cyclization: One-Pot Access to Blue-Emitting Phenanthrone-Type Polyheterocycles
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Disclosed herein is a highly efficient one-pot synthetic strategy to phenanthrone-type polyheterocycles via tandem rhodium(III)-catalyzed ortho-C-H heteroarylation of indolyl ketones and copper(II)-promoted intramolecular cyclization. This protocol enables a library of blue-emitting fluorophores with high quantum yields and narrow full widths at half-maximum to be rapidly built from readily available substrates, among of which 6,6,7,9,12-pentamethyl-6,12-dihydro-5H-benzofuro[2,3-a]carbazol-5-one (4a) exhibits pure blue emission with Commission Internationale de I'Eclairage coordinates of (0.15, 0.09) and a high quantum yield of 85% in CH2Cl2 solution.
- Pu, Xingwen,Zhang, Mangang,Lan, Jingbo,Chen, Shuyou,Liu, Zheng,Liang, Wenbo,Yang, Yudong,Zhang, Min,You, Jingsong
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supporting information
p. 1139 - 1143
(2019/05/16)
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- N -aminopyridinium salts as precursors for N-centered radicals - Direct amidation of arenes and heteroarenes
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Readily prepared N-aminopyridinium salts are valuable precursors for the generation of N-centered radicals. Reduction of these salts by single electron transfer allows for clean generation of amidyl radicals. It is shown that direct radical C-H amination of heteroarenes and arenes can be achieved with N-aminopyridinium salts under mild conditions by using photoredox catalysis.
- Greulich, Tobias W.,Daniliuc, Constantin G.,Studer, Armido
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supporting information
p. 254 - 257
(2015/03/05)
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- A selective, tin-free radical mediated synthesis of indoles based on a sulfonate template
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A synthesis of indoles based on a vinyl sulfonate template is described. The approach employs a sulfonate group which plays three discrete roles in the synthetic sequence. Firstly the highly electron-withdrawing sulfonate group behaves as an activating group for a 1,4-addition of an aniline to the unsaturated system. Secondly, the electron-withdrawing nature of the same group also allows it to behave as a radical stabilising group which facilitates radical cyclisation to an aromatic ring to yield a transient indoline. Finally, the pendant sulfonate group behaves as a leaving group to yield the indole.
- Gray, Vincent James,Wilden, Jonathan D.
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supporting information; experimental part
p. 41 - 44
(2012/01/05)
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- 5-PYRIDIN-3-YL-1,3-DIHYDRO-INDOL-2-ON DERIVATIVES AND THEIR USE AS MODULATORS OF ALDOSTERONE SYNTHASE AND/OR CYP11B1
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The present invention provides a compound a formula (I); or a pharmaceutically acceptable salt thereof, wherein: X is CH2, O, S or-NR1; each R1 are independently C1-7alkyl or C3-8cycloalkyl; each of R
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Page/Page column 90
(2010/12/17)
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- The effect of substitution on the utility of piperidines and octahydroindoles for reversible hydrogen storage
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Substituted piperidines and octahydroindoles are compared in terms of their usability as reversible organic hydrogen storage liquids for hydrogen-powered fuel cells. Theoretical Gaussian calculations indicate which structural features are likely to lower the enthalpy of dehydrogenation. Experimental results show that attaching electron donating or conjugated substituents to the piperidine ring greatly increases the rate of catalytic dehydrogenation, with the greatest rates being observed with 4-aminopiperidine and piperidine-4-carboxamide. Undesired side reactions were observed with some compounds such as alkyl transfer reactions during the dehydrogenation of 4-dimethylaminopiperidine, C-O and C-N cleavage reactions during hydrogenation and/or subsequent dehydrogenation of 4-alkoxy and 4-amino indoles, and disproportionation during the hydrogenation of 4-aminopyridine. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Cui, Yi,Kwok, Samantha,Bucholtz, Andrew,Davis, Boyd,Whitney, Ralph A.,Jessop, Philip G.
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p. 1027 - 1037
(2008/12/20)
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- Highly efficient construction of benzene ring in carbazoles by palladium-catalyzed endo-mode oxidative cyclization of 3-(3′-alkenyl) indoles
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A highly efficient construction of the benzene ring in carbazoles by palladium-catalyzed endo-mode oxidative cyclization of 3-(3′-alkenyl)- indoles was developed. The reaction utilizes benzoquinone as the stoichiometric oxidant and is conducted under mild conditions.
- Kong, Aidi,Han, Xiuling,Lu, Xiyan
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p. 1339 - 1342
(2007/10/03)
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- Direct palladium-catalyzed C-2 and C-3 arylation of indoles: A mechanistic rationale for regioselectivity
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We have recently developed palladium-catalyzed methods for direct arylation of indoles (and other azoles) wherein high C-2 selectivity was observed for both free (NH)-indole and (NR)-indole. To provide a rationale for the observed selectivity ("nonelectrophilic" regioselectivity), mechanistic studies were conducted, using the phenylation of 1-methylindole as a model system. The reaction order was determined for iodobenzene (zero order), indole (first order), and the catalyst (first order). These kinetic studies, together with the Hammett plot, provided a strong support for the electrophilic palladation pathway. In addition, the kinetic isotope effect (KIEH/D) was determined for both C-2 and C-3 positions. A surprisingly large value of 1.6 was found for the C-3 position where the substitution does not occur (secondary KIE), while a smaller value of 1.2 was found at C-2 (apparent primary KIE). On the basis of these findings, a mechanistic interpretation is presented that features an electrophilic palladation of indole, accompanied by a 1,2-migration of an intermediate palladium species. This paradigm was used to design new catalytic conditions for the C-3 arylation of indole. In case of free (NH)-indole, regioselectivity of the arylation reaction (C-2 versus C-3) was achieved by the choice of magnesium base.
- Lane, Benjamin S.,Brown, Meghann A.,Sames, Dalibor
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p. 8050 - 8057
(2007/10/03)
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- Direct C-H bond arylation: Selective palladium-catalyzed C2-arylation of N-substituted indoles
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(Equation Presented) We present a new, practical method by which N-substituted indoles may be selectively arylated in the C2-position with good yields, low catalyst loadings, and a high degree of functional group tolerance. Our investigation found that two competitive processes, namely, the desired cross-coupling and biphenyl formation, were operative in this reaction. A simple kinetic model was formulated that proved to be instructive and provided useful guidelines for reaction optimization; the approach described within may prove to be useful in other catalytic cross-coupling processes.
- Lane, Benjamin S.,Sames, Dalibor
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p. 2897 - 2900
(2007/10/03)
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- Inhibitors of Protein Kinase C. 1. 2,3-Bisarylmaleimides
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The design and synthesis of a series of novel inhibitors of protein kinase C (PKC) is described.These 2,3-bisarylmaleimides were derived from the structural lead provided by the indolocarbazoles, staurosporine and K252a.Optimum activity required the imide NH, both carbonyl groups, and the olefinic bond of the maleimide ring. 2,3-Bisindolylmaleimides were the most active, and the potency of these was improved by a chloro substituent at the 5-position of one indole ring (compound 28, IC50 0.11 μM).In a series of (phenylindolyl)maleimides, nitro compound 74 was most active (IC50 0.67 μM).Naphthalene 19 and benzothiophene 21 showed greater than 100-fold selectivity for inhibition of PKC over the closely related cAMP-dependent protein kinase (PKA).
- Davis, Peter D.,Hill, Christopher H.,Lawton, Geoffrey,Nixon, John S.,Wilkinson, Sandra E.,et al.
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p. 177 - 184
(2007/10/02)
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