10257-92-8Relevant articles and documents
Palladium-catalyzed direct C2-arylation of free (N–H) indoles via norbornene-mediated regioselective C–H activation
Gao, Yadong,Zhu, Wangying,Yin, Long,Dong, Bo,Fu, Jingjing,Ye, Zhiwen,Xue, Fengtian,Jiang, Chao
, p. 2213 - 2216 (2017)
A palladium-catalyzed direct C2-arylation reaction of free (N–H) indoles has been developed. This reaction relies on a norbornene-mediated C–H activation process on the indole ring, which features high regioselectivity and excellent functional group tolerance.
Titanium-induced syntheses of furans and indoles
Furstner,Jumbam,Weidmann
, p. 6695 - 6696 (1991)
Aromatic acyloxycarbonyl- and acylamidocarbonyl compounds on treatment with titanium on graphite (4 equivalents) readily afford (benzo)furans and indoles respectively, by an unprecedented McMurry-type reaction.
A practical one-pot synthesis of 2,3-disubstituted indoles from unactivated anilines
Tokunaga, Makoto,Ota, Mitsuru,Haga, Masa-aki,Wakatsuki, Yasuo
, p. 3865 - 3868 (2001)
2-Substituted-3-methyl indoles are synthesized with good regioselectivity from readily available substrates and catalysts, i.e. the reaction of anilines with propargyl alcohols in the presence of 0.36-1 mol% Ru3(CO)12.
3-Methyl-2-phenyl-1-substituted-indole derivatives as indomethacin analogs: Design, synthesis and biological evaluation as potential anti-inflammatory and analgesic agents
Abdellatif, Khaled R. A.,Lamie, Phoebe F.,Omar, Hany A.
, p. 318 - 324 (2016)
In a new group of 3-methyl-2-phenyl-1-substituted-indole derivatives (10a-f), the indomethacin analogs were prepared via the Fisher indole synthesis reaction of propiophenone with appropriately substituted phenylhydrazine hydrochloride. This is followed by the insertion of the appropriate benzyl or benzoyl fragment. All the synthesized compounds were evaluated for their anti-inflammatory (in vitro and in vivo) and analgesic activities. The methanesulphonyl derivatives 10d, e and f showed the highest anti-inflammatory (in vitro and in vivo) and analgesic activities. In addition, molecular docking studies were performed on compounds 10a-f and the results were in agreement with that obtained from the in vitro COX inhibition assays. The significant anti-inflammatory and analgesic activities exhibited by 10d and 10e warrant continued preclinical development as potential anti-inflammatory and analgesic agents.
Palladium/Copper Cocatalyzed Coupling Reaction of Aroyl Hydrazides with Indoles
Liu, Congrong,Yang, Fulai
, p. 1213 - 1217 (2016)
An unprecedented palladium/copper cocatalyzed coupling reaction of indoles with simple aroyl hydrazides has been developed under aerobic conditions. A range of aroyl hydrazides underwent palladium/copper cocatalyzed oxidative arylation with indoles open to air in a 1:1 mixture of dimethyl sulfoxide and nitromethane to give structurally diverse 2-arylindoles or 3-arylindoles in moderate to good yields. The reaction well tolerates a wide variety of functional groups such as alkoxy, halo, ester.
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Kissman et al.
, p. 3948 (1952)
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Gas-phase thermolysis of benzotriazole derivatives: Part 1 - Synthesis of α-N(1)- and N(2)-benzotriazolyl ketones and kinetics and mechanism of their gas-phase pyrolysis
Dib, Hicham H.,Al-Awadi, Nouria A.,Ibrahim, Yehia A.,El-Dusouqui, Osman M.E.
, p. 267 - 272 (2004)
1-(Benzotriazol-1-yl)propan-2-one (1) and 3-(benzotriazol-1-yl)butan-2-one (2), and their respective phenyl analogues 2-(benzotriazol-1-yl)-1- phenylethanone (3) and 2-(benzotriazol-1-yl)-1-phenylpropan-1-one (4), together with 1-cyanobenzotriazole (5) and 1-(benzotriazol-2-yl)propan-2-one (6), were synthesized and then subjected to gas-phase thermolysis. The products of complete pyrolysis of 1-4 were found to be aniline in addition to either 2-substituted indoles or 2,3-disubstituted indoles. The kinetics of the gas-phase thermal elimination reactions of the present compounds were also studied, the first such investigation on benzotriazoles. The Arrhenius preexponential factor (A/s-1) and activation energy (Ea/kJ mol-1) are, respectively: 10.03 and 156.7 for (1), 9.93 and 158.0 for (2), 12.68 and 169.9 for (3), 9.45 and 144.4 for (4) and 15.40 and 163.6 for (5). Compound 6 appeared to have isomerized by a thermally allowed 1,5-group migration into 1 prior to thermolysis. The results of the kinetic and product analysis are rationalized with reference to a mechanism involving extrusion of a stable (N2) molecule and formation of a reactive 1,3-biradical intermediate, which in turn rearranges into the final products of reaction. 2004 John Wiley & Sons, Ltd.
Iridium- and ruthenium-catalysed synthesis of 2,3-disubstituted indoles from anilines and vicinal diols
Tursky, Matyas,Lorentz-Petersen, Linda L. R.,Olsen, Lasse B.,Madsen, Robert
, p. 5576 - 5582 (2010)
A straightforward and atom-economical method is described for the synthesis of 2,3-disubstituted indoles. Anilines and 1,2-diols are condensed under neat conditions with catalytic amounts of either [Cp*IrCl2] 2/MsOH or RuCl3·xH2O/phosphine (phosphine = PPh3 or xantphos). The reaction does not require any stoichiometric additives and only produces water and dihydrogen as byproducts. Anilines containing methyl, methoxy, chloro and fluoro substituents can participate in the cyclocondensation. Meta-substituted anilines give good regioselectivity for 6-substituted indoles, while unsymmetrical diols afford excellent regioselectivity for the indole isomer with an aryl or large alkyl group in the 2-position. The mechanism for the cyclocondensation presumably involves initial formation of the α-hydroxyketone from the diol. The ketone subsequently reacts with aniline to generate the α-hydroxyimine which rearranges to the corresponding α-aminoketone. Acid- or metal-catalysed electrophilic ring-closure with the release of water then furnishes the indole product.
Catalytic Asymmetric N-Alkylation of Indoles and Carbazoles through 1,6-Conjugate Addition of Aza-para-quinone Methides
Chen, Min,Sun, Jianwei
, p. 4583 - 4587 (2017)
Catalytic asymmetric N-alkylation of indoles and carbazoles represents a family of important but underdeveloped reactions. Herein, we describe a new organocatalytic strategy in which in situ generated aza-para-quinone methides are employed as the alkylating reagent. With the proper choice of a chiral phosphoric acid and an N-protective group, the intermolecular C?N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional-group compatibility. Control experiments and kinetic studies provided important insight into the reaction mechanism.
1,2-Disubstituted 1,2-Dihydro-1,2,4,5-tetrazine-3,6-dione as a Dynamic Covalent Bonding Unit at Room Temperature
Ikeda, Kazuki,Kabasawa, Akira,Kakugo, Akira,Kawai, Kentaro,Kojima, Masahiro,Kokado, Kenta,Matsunaga, Shigeki,Sada, Kazuki,Sato, Akane,Yoshino, Tatsuhiko
supporting information, p. 1370 - 1379 (2022/02/01)
Dynamic covalent bonds are useful tools in a wide range of applications. Although various reversible chemical reactions have been studied for this purpose, the requirement for harsh conditions, such as high temperature and low or high pH, to activate generally stable covalent bonds limits their potential applications involving biomolecules or household utilization. Here, we report the design, synthesis, characterization, and dynamic covalent bonding properties of 1,2-disubstituted 1,2-dihydro-1,2,4,5-tetrazine-3,6-dione (TETRAD). Hetero-Diels–Alder reactions of TETRAD with furan derivatives and their retro-reactions proceeded rapidly at room temperature under neutral conditions, enabling a chemically induced sol–gel transition system.
Tris-NHC-propagated self-supported polymer-based Pd catalysts for heterogeneous C-H functionalization
Choudhury, Joyanta,Dutta, Tapas Kumar,Mandal, Tanmoy,Mohanty, Sunit
supporting information, p. 10182 - 10185 (2021/10/12)
Three-dimensionally propagated imidazolium-containing mesoporous coordination polymer and organic polymer-based platforms were successfully exploited to develop single-site heterogenized Pd-NHC catalysts for oxidative arene/heteroarene C-H functionalization reactions. The catalysts were efficient in directed arene halogenation, and nondirected arene and heteroarene arylation reactions. High catalytic activity, excellent heterogeneity and recyclability were offered by these systems making them promising candidates in the area of heterogeneous C-H functionalization, where efficient catalysts are still scarce.
