- Diastereoselective synthesis of functionalised carbazoles via a sequential Diels-Alder/ene reaction strategy
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An operationally simple one-pot, three-component, diastereoselective synthesis of saturated carbazoles and related pyridazino[3,4-b]indoles, based on two sequential intermolecular pericyclic reactions, is described. The reaction sequence involves an intermolecular Diels-Alder (D-A) reaction of a 3-vinyl-1H-indole, containing an electron withdrawing N-protecting group, with a suitable dienophile. Due to the electron withdrawing nature of the N-protecting group the resultant D-A cycloadducts are sufficiently stabilised to allow for a subsequent in situ diastereospecific intermolecular ene reaction to take place with an added enophile, generating functionalised carbazoles with relative stereocontrol of up to four stereocentres.
- Cowell, Joseph,Abualnaja, Matokah,Morton, Stephanie,Linder, Ruth,Buckingham, Faye,Waddell, Paul G.,Probert, Michael R.,Hall, Michael J.
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p. 16125 - 16152
(2015/03/04)
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- Access to biaryl sulfonamides by palladium-catalyzed intramolecular oxidative coupling and subsequent nucleophilic ring opening of heterobiaryl sultams with amines
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The installation of sulfonamide pharmacophores on heterobiaryls has successfully been executed by a previously unknown palladium-catalyzed intramolecular oxidative coupling in N-arylsulfonyl heterocycles followed by novel ring opening of heterobiaryl sultams with amine nucleophiles. The protocol has a wide scope of substrates warranting broad applications in the synthesis of heterobiaryls containing an o-sulfonyl or carboxyl functional group.
- Laha, Joydev K.,Dayal, Neetu,Jethava, Krupal P.,Prajapati, Dilip V.
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supporting information
p. 1296 - 1299
(2015/03/14)
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- Gold(I)-catalyzed dearomative rautenstrauch rearrangement: Enantioselective access to cyclopenta[ b ]indoles
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A highly enantioselective dearomative Rautenstrauch rearrangement catalyzed by cationic (S)-DTBM-Segphosgold(I) is reported. This reaction provides a straightforward method to prepare enantioenriched cyclopenta[b]indoles. These studies show vast differenc
- Zi, Weiwei,Wu, Hongmiao,Toste, F. Dean
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supporting information
p. 3225 - 3228
(2015/03/30)
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- Organocatalytic asymmetric Michael addition of aliphatic aldehydes to indolylnitroalkenes: Access to contiguous stereogenic tryptamine precursors
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Because of the importance of the indole framework and the versatile transformation of nitro and formyl groups, the efficient synthesis of optically pure 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanals, one type of tryptamine precursors are of great interest for pharmaceutical and biological research. Herein, the Michael addition of aliphatic aldehydes to indolylnitroalkenes has been developed using (S)-diphenylprolinol trimethylsilyl ether as an organocatalyst, which provides the desired optically pure syn 2-alkyl-3-(1H-indol-3-yl)-4-nitrobutanal derivatives in up to 98% yield with up to >99:1 dr and >99% ee. To show the synthetic usefulness of this methodology, optically active 2-alkyl-4-nitro-3-(1-tosyl-1H-indol-3-yl)butan-1- ol and tryptamine derivatives are readily obtained by stepwise systematic transformations.
- Chen, Jian,Geng, Zhi-Cong,Li, Ning,Huang, Xiao-Fei,Pan, Feng-Feng,Wang, Xing-Wang
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p. 2362 - 2372
(2013/05/21)
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- Total synthesis of (±)-hyrtiazepine
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The total synthesis of the azepinoindole alkaloid, (±)-hyrtiazepine, was achieved. Construction of the azepinoindole core structure was carried out by C-4 selective α-hydroxyalkylation of 5-hydroxyindole, introduction of serine at C-3 of the indole moiety, and intramolecular imination.
- Ito, Fumihiro,Shudo, Koichi,Yamaguchi, Kentaro
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experimental part
p. 1805 - 1811
(2011/04/16)
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- N-ARYLSULFONYL-3-SUBSTITUTED INDOLES HAVING SEROTONIN RECEPTOR AFFINITY, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM
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The present invention relates to novel N-arylsulfonyl-3-substituted indole compounds, their derivatives, their analogs, their tautomeric forms, their stereoisomers, their geometric forms, their N-oxides, their polymorphs, their pharmaceutically acceptable
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- Synthesis and serotonin receptor affinities of a series of trans-2- (indol-3-yl)cyclopropylamine derivatives
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A series of four racemic ring-substituted trans-2-(indol-3- yl)cyclopropylamine derivatives was synthesized and tested for affinity at the 5-HT(1A) receptor, by competition with [3H]-8-OH-DPAT in rat hippocampal homogenates, and for affinity at
- Vangveravong, Suwanna,Kanthasamy, Arthi,Lucaites, Virginia L.,Nelson, David L.,Nichols, David E.
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p. 4995 - 5001
(2007/10/03)
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- Structure function relationship study of yuehchukene. I. Anti-implantation and estrogenic activities of substituted yuehchukene derivatives
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(+/-)-Yuehchukene (YCK) is a novel bis-indole alkaloid with potent anti-implantation activity in rats.The present paper reports the activity of YCK derivatives by substitution on the parent compound.Substitutions on the indole nitrogens or on 2- and 5'-positions of the indole moiety abolished activity.N-1'-methylation of the free indole only permitted a 30percent residual activity.Saturation of the C9-C10 cyclohexenyl double bond did not affect activity at all.Hydroxylation, whether on the C9-C10 double bond, or at C2 or C5, rendered the hydroxylated derivatives inactive.This suggests that the active metabolite in anti-implantation was probably not a hydroxylated derivative carrying estrogenic activity.
- Chan, WL,Ho, DD,Lau, CP,Wat, KH,Kong, YC,et al.
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p. 387 - 394
(2007/10/02)
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