Catalytic, enantioselective hydroacylations of N-allylindole-2-carboxaldehydes and N-allylpyrrole-2-carboxaldehydes are reported. In contrast to many alkene hydroacylations that form six-membered rings, these annulative processes occur in the absence of ancillary functionality to stabilize the acylrhodium(III) hydride intermediate. The intramolecular hydroacylation reactions generate 7,8-dihydr...

The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptak...

TFA alone was found to be remarkably effective for the intramolecular hydroarylation (IMHA) of alkynes when employed as a solvent in the cyclization of 3-alkynyl substituted 2-(indol-3-yl)quinoxalines. This simple and metal free cyclization method afforded a range of indolophenazines as new and potential cytotoxic agents. The use of excess TFA was found to be crucial for the success of this rea...

When indole was incubated under methanogenic conditions with an inoculum of sewage sludge, the chemical was metabolized with 10 days and temporary formation of an intermediate was observed. The metabolite was isolated by thin-layer chromatography and determined to be 1,3-dihydro-2H-indol-2one (oxindole) by UV spectroscopy (lambdaMAX, 247 nm) and mass spectrometry (m/z, 133). The methane produce...

In the present work, a series of new N’-[{5-(4-aryl) 1,3-thiazol-2yl}carbohydrazide-methyl]- 3(4-arylimino) indol-2-one analogs (5a-g) had heen synthesized from 3-(4-arylimino)-2-oxo- 1-indole-acetylthiosemicarbazide (4a-g) in ethanol, in the presence of phenacyl bromide or substituted phenacyl bromides. The compound 5e was characterized by its elemental analysis, IR, 1 HNMR and Mass Spectrosco...

In the present work, a series of new 5-substituted-3-(4-arylimino)-1-[5-mercapto(1,3,4-oxadiazolyl)]-methyl-indol-2-one (4a-g) have been synthesized by heterocyclization of 5-substituted-3-(4-arylimino)-2-oxo-1-indole acetylhyrazide (3a-g) on treatment with CS2 in ethanolic KOH. The compound 4a was characterized by its elemental analysis, IR, 1HNMR and Mass Spectroscopy. The synthesized compoun...

A series of nine novel 3-tetrazolylmethyl-azepino[4,5-b]indol-4-ones were prepared in moderate to good overall yields in only two reaction steps. The first step consisted of a one-pot sequential process of an Ugi-azide multicomponent reaction, N-acylation and SN2 to give the xanthates. The second step was an intramolecular cyclization under free radical conditions. Also, their binding modes hav...

Ethyl 2-[2-(4-nitrobenzoyl)-1H-indol-3-yl]acetate was prepared in good yield and characterized by the aza-alkylation/intramolecular Michael cascade reaction of (E)-ethyl 3-[2-(tosylamino)phenyl]acrylate with 2-bromo-4′ ′-nitroacetophenone, followed by desulfonative dehydrogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) The structure of the newly synthesized compound was determined using ...

An efficient and convenient method to synthesize highly functionalized 3,7'-bisindole derivatives has been developed via a Michael addition and cyclic condensation reaction of heterocyclic ketene aminals (HKAs) with 2-(1H-indol-3-yl)cyclohexa-2,5-diene-1,4-dione derivatives in ethanol-based solvents at room temperature. This strategy provides an efficient, environmentally friendly approach for ...

In the title compound, C(15)H(11)N(3)O(4)S, the dihedral angle between the mean planes of the dihydro-indol-2-one (r.m.s. deviation = 0.015 Å) and dihydro-thieno[3,2-b]pyran (r.m.s. deviation = 0.011 Å) ring systems is 89.53 (3)°. The crytal packing is consolidated by inter-molecular N-H⋯O and N-H⋯N hydrogen bonds, which link the mol-ecules into a two-dimensional network into sheets lying paral...