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A novel method to synthesise 2-arylindoles is demonstrated via direct arylation of indoles with arylsulfonyl hydrazides. Under the optimized reaction conditions, the reaction well tolerates a wide variety of functional groups to afford structurally diverse 2-arylindoles in good to excellent yields at 70 C.

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A visible light-induced photocatalytic intramolecular cyclization of styryl azides has been developed in the presence of the ruthenium complex Ru(bpy)3Cl2 (0.5 mol%) as photocatalyst at room temperature. The present photocatalytic strategy features operational simplicity as well as high functional group tolerance, and provides a facile access to various 2-substituted N-free indoles in good to excellent yields. Importantly, the present process can employ sunlight as the light source to afford the corresponding products without loss of reaction efficiency.

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Ethyl-5-O-chloroacetyl-2-methylindole-3-carboxylates (2a-e) have been synthesised by the reaction of ethyl 5-hydroxy-2-methylindole-3-carboxylates (1a-e) with chloroacetyl chloride in dry benzene containing triethylamine.These indoles (2a-e) on condensation with methylpiperazine in dry acetone in the presence of anhydrous K2CO3, afford ethyl 5-O-(4-methylpiperazin-1-ylacetyl)-2-methylindole-3-carboxylates (3a-e).Compounds 3a-e are converted into their oxalate derivatives (4a-e).Indole-3-glyoxyl chlorides (6a-e) have been prepared from appropriate indoles (5a-e) byreaction with oxalyl chloride in dry ether. these derivatives on condensation with methylpiperazine yield 3-(4-methyl-1-piperazinylglyoxylyl)indoles (7a-e) wich are converted into oxalate salts (8a-e).Compounds 4a-e and 8a-e have been screened for their antiserotonin activity.Only compound 4d is found to exhibit antiserotonin activity.

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The C-C ring closure of alpha-chloromethyl alkyl or aryl N-aryl imines catalyzed with 1 to 10 % Pd(OAc)2/P(p-tolyl)3 afford efficiently 2-aryl- and 2-alkyl-1H-indoles. The heterocyclization reaction involves the initial formation of [2-(arylimino)ethyl]palladium(II) chloride complexes with subsequent C-H activation of the aromatic amine ring. Readily or commercially available alpha-chloromethyl-aryl or -alkyl ketones are used as the precursors. Functionalized indoles at the benzene ring are obtained when the imines are derived from substituted anilines.

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A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.

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A series of (3R*,5S*)-omega-substituted-3-carboxy-3,5-dihydroxyalkanoic acids have been synthesized and evaluated as inhibitors of the recombinant human form of ATP-citrate lyase. The best of these have K(i)’s in the 200- 1000 nM range. As the corresponding thermodynamically favored gamma-lactone prodrugs, a number of compounds are able to inhibit cholesterol and fatty acid synthesis in HepG2 cells and reduce plasma triglyceride levels in vivo. The best of these, compound 77, is able to induce clear hypocholesterolemic and hypotriglyceridaemic responses when administered orally to rat and dog. These results provide evidence to support the hypothesis that compounds which inhibit ATP-citrate lyase have the potential to be a novel class of hypolipidemic agent, which possess combined hypocholesterolemic and hypotriglyceridemic activities.

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(Chemical Equation Presented) No compass required: A method is described for forming biaryl C-C bonds by a PdII-catalyzed cross-coupling of aryl C-H bonds with aryl boronic acids under mild conditions without the presence of directing groups. Different substituents on both (hetero)arenes and aryl boronic acids are compatible with the reaction conditions, and the homocoupling of boronic acids is highly inhibited. Dioxygen was applied as the final oxidant.

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Tandem multi-site cyclization triggered by Rh(III)-catalyzed C-H activation has been achieved for highly efficient synthesis of spirocycle indolin-3-one (C2-cyclization), benzo[a]carbazole (C3-cyclization) and an unusual indoxyl core (N1-cyclization). In particular, the synthesis of pseudo-indoxyl is typically completed within 10 min, and the reaction tolerates air, water and a range of solvents.

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The oxidative kinetic resolution of 2-substituted indoline derivatives was achieved by hydrogen transfer to imines by means of a chiral phosphoric acid catalyst. The oxidative kinetic resolution was applicable to racemic alkyl- or aryl-substituted indolines, and the remaining indolines were obtained in good yields with excellent enantioselectivities.

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A facile and efficient asymmetric dearomative oxyalkylation of indoles with TEMPO oxoammonium salt and a variety of aldehydes and ketones has been described. This metal-free approach provides a straightforward access to C2 quaternary oxindoles in high yields with excellent diastereo- and enantioselectivities under very mild conditions. The reaction goes smoothly even with only 0.1% equivalent catalyst. Moreover, 2-alkylindoles have proven to be suitable substrates for the first time.

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