- Exploiting a novel size exclusion phenomenon for enantioselective acid/base cascade catalysis
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A novel size exclusion phenomenon between PS-BEMP and sterically bulky BPAs, has been discovered and exploited in a one-pot base-catalysed Michael addition/acid-catalysed enantioselective N-acyliminium cyclisation cascade, allowing the preparation of structurally complex β-carbolines with moderate to good enantiocontrol.
- Muratore, Michael E.,Shi, Lei,Pilling, Adam W.,Storer, R. Ian,Dixon, Darren J.
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supporting information; experimental part
p. 6351 - 6353
(2012/07/17)
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- Reaction pathway in the vapour-phase synthesis of indole and alkylindoles
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The vapour-phase synthesis of indole and its derivatives from aniline or alkylanilines and ethylene glycol or other diols was investigated with the use of a novel ZrO2/SiO2 (5:95 w/w) catalyst to check the applicability of this synthesis to a wide number of alkylindoles. During feeding with alkylaniline, the above catalyst showed catalytic results better than those reported in the literature, and a very good regenerability. In particular, with ethylene glycol, the best yields in the corresponding indoles were obtained when a C2-C3 alkyl chain was located in the ortho position to the amino group. The differences in reactivity between aniline and alkylaniline were significantly reduced when the length of the diol chain was increased and eliminated with 2,3-butanediol. On the basis of the above data and those collected sharing the synthesis in single steps, a possible overall reaction pathway was proposed to design a better tailor-made catalyst. It was also indicated that the formation of heavy compounds, which are able to deactivate the catalyst, were not derived from the reagents or the following reactions on the indole formed, but might be mainly attributed to the polycondensation of an aldehyde intermediate.
- Campanati,Franceschini,Piccolo,Vaccari
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- Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles
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Anilines react with alkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180°C in the presence of a catalytic amount of a ruthenium catalyst together with SnCl2·2H2O to afford the corresponding indoles in moderate to good yields. Especially, when triisopropanolammonium chloride is employed to react with anilines, 2-methylindoles are formed regioselectively. The presence of SnCl2·2H2O is necessary for the effective formation of indoles. A reaction pathway involving alkanol group transfer from alkanolamines to anilines, N-alkylation of anilines by anilinoalkanols and heteroannulation of 1,2-dianilinoalkanes is proposed for this catalytic process.
- Cho, Chan Sik,Kim, Jin Hwang,Kim, Tae-Jeong,Shim, Sang Chul
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p. 3321 - 3329
(2007/10/03)
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- Ruthenium-catalyzed synthesis of indoles from anilines and trialkanolammonium chlorides in an aqueous medium
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Anilines react with trialkanolammonium chlorides in an aqueous medium (H2O-dioxane) at 180°C in the presence of a catalytic amount of ruthenium(III) chloride hydrate and triphenylphosphine together with tin(II) chloride dihydrate to afford the corresponding indoles in good yields. (C) 2000 Elsevier Science Ltd.
- Cho, Chan Sik,Kim, Jin Hwang,Shim, Sang Chul
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p. 1811 - 1814
(2007/10/03)
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- Preparation of indole and indole derivatives
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Indole and indole derivatives are prepared by contacting under mild reaction conditions an N-(2-toly)formidate, N-(3-methyl-2-pyridyl)formimidate, or N-methyldiazyl formimidate with an alkali metal amide.
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- Process for the production of 7-ethyl indole
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Process for the production of 7-ethyl indole by dehydrocyclization of 2,6-diethylaniline and then partial hydrogenation of the accumulated raw product.
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- Studies on Several 7-Substituted N,N-Dimethyltryptamines
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Several 7-substituted derivatives of N,N-dimethyltryptamine (DMT) were prepared and evaluated in the rat fundus serotonin receptor assay and in a behavioral (discriminative stimulus) assay in rats.Both 7-Me- and 5-Ome-7-Me-DMT possess a higher pA2, and 5,7-(OMe)2-DMT a lower pA2, than that of DMT itself.Like DMT, all three of these compounds produce behavioral effects in rats which are similar to those of the hallucinogen 5-OMe-DMT.Although 7-Et- and 7-Br-DMT possess a higher serotonin receptor affinity than DMT, neither produce behavioral effects which parallelthose of 5-OMe-DMT.In contrast, 6-OMe-DMT and its 5-OMe derivative do not interact with the serotonin receptors in a competitive manner and are inactive in the discriminative stimulus assay.
- Glennon, R. A.,Schubert, E.,Jacyno, J. M.,Rosecrans, J. A.
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p. 1222 - 1226
(2007/10/02)
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