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A simple method for the synthesis of various 3-(4,5-dihydro-1H-imidazole-2-yl)-1H-indoles is described. Treatment of different substituted indoles with 1-acetyl-imidazolidin-2-one in the presence of phosphorus oxychloride afforded after hydrolysis in ethanol the corresponding 3-(4,5-dihydro-1H-imidazole-2-yl)-1H-indoles in moderate to good yields.

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2-Arylindoles were prepared by a sequential reaction of Ag-catalyzed alpha-addition-Pd-catalyzed C-H bond functionalization of tetrazoles with bromoalkynes. A stereocontrolled Ag-catalyzed alpha-addition reaction of tetrazoles with bromoalkynes underwent smoothly to generate (Z)-N-(2-bromo-1- vinyl)-N-arylcyanamides, which were subsequently converted into 2-arylindoles through an intramolecular cyclization by Pd-catalyzed direct C-H bond functionalizations.

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We report the synthesis and the affinity data at both the peripheral (PBR) and the central benzodiazepine receptors of a series of N,N-dialkyl-2-phenylindol-3-ylglyoxylamide derivatives III, designed as conformationally constrained analogues of 2-phenylindole-3-acetamides II such as FGIN-1-27. Most of the new compounds showed a high specificity and affinity for PBR, with Ki in the nanomolar to subnanomolar range. The most potent ligands (4-7, 9, 13-27) stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than that of classical ligands. The SARs of this new class of compounds are discussed.

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Hydroamination is an atom-economical reaction to form C-N bonds, which are ubiquitous in organic compounds. Hydroamination has seen prolific advancements and has mostly focused on the development of homogeneous catalysts based on lanthanides or transition metals. Here, we have developed silica-supported, site-isolated Zn(II) sites through a combined surface organometallic chemistry (SOMC) and thermolytic molecular precursor (TMP) approach and show that they catalyze the intramolecular hydroamination of alkynes. This material is applicable to a broad range of substrates. On the basis of kinetics and in situ IR spectroscopic studies, we propose that the mechanism involves coordination of the aminoalkyne onto Zn(II) followed by the heterolytic activation of the N-H bond and subsequent cyclization and proton transfer.

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An asymmetric normal-electron-demand aza-Diels-Alder cycloaddition of 2-aryl-3H-indol-3-ones and 2,4-dienals was explored via trienamine catalysis of a chiral secondary amine. Multifunctional tricyclic polyhydropyrido[1,2-a] indoles were efficiently constructed in good stereoselectivity (up to 92% ee, >19:1 dr).

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A series of unusual six-ring-fused heterocycles containing indole and quinoline skeletons was successfully synthesized by a copper-catalyzed reaction from 2-arylated indoles. Two new bonds were regioselectively formed from C-H and C-H coupling. 18O-Labelled experiments revealed that the dioxygen is not only the oxidant but also the reactant. Copyright

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A versatile route has been developed for the synthesis of 2-arylindoles using a Pd-catalyzed tandem process. Under reductive conditions, different 2-arylindoles were synthesized from phenylglyoxal and aniline. This synthetic methodology involves a tandem reaction of four steps with high regioselectivity. Alternatively, 2-anilinoacetophenones intermediates also can be using to give access to the corresponding 2-arylindoles.

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Versatile reactive activities of allyl alcohols with free indoles in C?H functionalization reactions were investigated. Direct alkylation or cascade cyclization reactions could be selectively controlled based on the catalyst system: Ru(PPh3)3Cl2 provided C3-substituted beta-ketone indoles whereas [Ru(p-cymene)Cl2]2 yielded cyclized indoles.

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In the past decades, C?H oxidative olefination of indole at C-2, C-3, C-4 and C-7 positions was well addressed. We report here a rhodium-catalyzed NH-indole-directed ortho C?H bond olefination of 2-arylindoles. This cross-dehydrogenative-coupling proved to be broad in substrate scope, tolerating a variety of functional groups. The synthesis of 6H-isoindolo[2,1-alpha]indoles via rhodium-catalyzed ortho C?H olefination and subsequent intramolecular aza-Michael reaction of 2-arylindoles was also demonstrated. (Figure presented.).

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The synthesis and in vitro evaluation of a number of N-acyltryptamines are reported. Structural changes include the N-acyl group and the 5- (H,CH3,Halogen), and 2- (Br, Ph) substituents. 5Br (6d) and 2,5-diBr (6j) proved to be high affinity melatonin agonists, thus proving that Br can substitute for the 5-OMe group without loss of affinity to melatonin receptors (mt1, MT2). 6j is the first example of a melatonin agonist devoid of the 5-OMe group and endowed with better affinity for mt1 and MT2 receptors than that of melatonin itself. SAR for selectivity and intrinsic activity of the title compounds were also drawn.

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