- SYNTHESIS OF 5-VINYLINDOLE BY SIMULTANEOUS DEHYDROGENATION AND DECARBOXYLATION OF 5-ETHYL-INDOLE-2-CARBOXYLIC ACID AND ITS ETHYL ESTER
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A new method is proposed for the synthesis of 5-vinylindole by simultaneous catalytic dehydrogenation and decarboxylation of 5-ethylindole-2-carboxylic acid and its ethyl ester, making it possible to more than double the yield of the previously described method.
- Starostenko, N. E.,Dat, Fung Tien,Serova, I. A.,Kamenetskii, A. V.,Suvorov, N. N.
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Read Online
- Magnesium catalyzed dephenylsulfonylation: Synthesis of 5-ethyl-1H-indole
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A novel magnesium metal catalyzed synthesis of 5-ethyl-1H-indole from 5-[2-(phenyl sulfonyl)ethyl]-1H-indole by dephenylsulfonylation mechanism providing an alternative and attractive approach to 5-ethyl-1H-indole with high yields. This approach is for both the protected and unprotected indoles.
- Rao, S. Venkat,Shrikant, H. Havale,Kumar, B. Sanjith,Krishna, G. Siva
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p. 2232 - 2234
(2017/10/05)
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- 5,5′-alkylsubsituted indigo for solution-processed optoelectronic devices
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A series of alkylated indigos were synthesized. Alkylated indigos were characterized by NMR, mass spectrometry, absorption spectra, cyclic voltammetry, and density functional theory (DFT) calculations. Propyl and butyl group substituted indigo was most soluble in chloroform and 1,2-dicrolobenzene, and these solubility were 65–89 times increased as compared to the parent indigo. DFT calculations suggested that the presence of the alkyl chains at the 5.5′-position increases the energy of the highest occupied molecular orbital, while reducing the energy of the lowest unoccupied molecular orbital. This theoretical finding was in good agreement with the experimental results. Crystal structures obtained by X-ray diffraction showed one-dimensional pi–pi stacking. Alkylated molecules were converted to leuco structure, and these structures were then converted to the corresponding indigos in the film state. After deposition of the films on TiO2/FTO substrate, oxidative photocurrents were observed.
- Watanabe, Motonori,Uemura, Naoki,Ida, Shintaro,Hagiwara, Hidehisa,Goto, Kenta,Ishihara, Tatsumi
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p. 4280 - 4287
(2016/07/06)
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- Direct B-alkyl Suzuki-Miyaura cross-coupling of trialkyl-boranes with aryl bromides in the presence of unmasked acidic or basic functions and base-labile protections under mild non-aqueous conditions
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An efficient and chemoselective palladium-catalyzed direct B-alkyl Suzuki-Miyaura cross-coupling of trialkylboranes with diversely functionalized aryl bromides is described. A wide variety of unmasked acidic or basic functions are tolerated. The mild non-
- Wang, Bing,Sun, Hui-Xia,Sun, Zhi-Hua,Lin, Guo-Qiang
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experimental part
p. 415 - 422
(2009/10/23)
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- Synthesis and biological evaluation of new dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, substituted with various saturated and unsaturated side chains via palladium catalyzed cross-coupling reactions
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The syntheses of a series of dipyrrolo[3,4-a:3,4-c]carbazole-1,3,4,6-tetraones, substituted in 10-position with saturated and unsaturated side chains, via palladium catalyzed cross-coupling reactions, are described. These compounds can be considered as granulatimide bis-imide analogues. Their inhibitory activity toward Chk1 kinase and their antiproliferative activities in vitro in four tumor cell lines are reported.
- Henon, Helene,Anizon, Fabrice,Golsteyn, Roy M.,Leonce, Stephane,Hofmann, Robert,Pfeiffer, Bruno,Prudhomme, Michelle
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p. 3825 - 3834
(2007/10/03)
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- PPAR ACTIVE COMPOUNDS
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Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.
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- PPAR active compounds
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Compounds are described that are active on PPARs, including pan-active compounds. Also described are methods for developing or identifying compounds having a desired selectivity profile.
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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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- Binding of O-alkyl derivatives of serotonin at human 5-HT1Dβ receptors
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In humans, 5-HT1D serotonin receptors represent terminal autoreceptors, and there is some evidence that 5-HT1D ligands may be useful in the treatment of migraine. The most widely used 5-HT1D agonist is sumatriptan; however, this agent reportedly displays little selectivity for 5-HT1D versus 5-HT1A receptors. To identify novel serotonergic agents with enhanced 5-HT1D versus 5-HT1A selectivity, we attempted to take advantage of possible differences in the regions of bulk tolerance associated with the 5-position of the 5-HT binding sites for these two populations of receptors. Examination of a series of 5-(alkyloxy)tryptamine derivatives demonstrated that compounds with unbranched alkyl groups of up to eight carbon atoms bind with high affinity at human 5-HT1Dβ receptors (K(i) 300-fold). Branching of the alkyl chain, to 5-[(7,7-dimethylheptyl)oxy]tryptamine (15), results in an agent with somewhat lower affinity (5-HT1Dβ K(i) = 2.3 nM) but with greater (i.e., 400-fold) 5-HT1D versus 5-HT1A selectivity. Replacement of the oxygen atom of 10 with a methylene group (i.e., 20), replacement of the O-proximate methylene with a carbonyl group (i.e., ester 26), or cyclization of the aminoethyl moiety to a carbazole (e.g., 34, 36) or β- carboline (i.e., 37), result in reduced affinity and/or selectivity. None of the compounds examined displayed significant selectivity for 5-HT1Dβ versus 5-HT1Dα sites; nevertheless, compounds 10 (recently shown to behave as a 5- HT1D agonist) and 15 represent the most 5-HT1D versus 5-HT1A selective agents reported to date.
- Glennon, Richard A.,Hong, Seoung-Soo,Bondarev, Mikhail,Law, Ho,Dukat, Malgorzata,Rakhit, Suman,Power, Patricia,Fan, Ermei,Kinneau, Diana,Kamboj, Rajender,Teitler, Milt,Herrick-Davis, Katharine,Smith, Carol
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p. 314 - 322
(2007/10/03)
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- SYNTHESIS OF 5-VINYLINDOLE
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A convenient method was developed for the synthesis of previously undescribed 5-vinylindole by catalytic dehydrogenation of 5-ethylindole.The effects of the temperature, the amount of catalyst, and the concentration of 5-ethylindole on the yield of the reaction products were investigated.The possibility of obtaining the 5-ethylindole used for dehydrogenation by heterogeneous-catalytic indolization of acetaldehyde p-ethylphenylhydrazone at aluminium oxide was investigated, and favourable conditions were found for this process.
- Suvorov, N. N.,Starostenko, N. E.,Zeiberlikh, F. N.
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p. 2236 - 2241
(2007/10/02)
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