2-Phenyl indoles

A variety of 2-substituted indoles can be prepared by the Gassman process. For example, when methyl phenacyl sulfide 22 was employed with aniline, the 2-phenyl indole was obtained in 81% yield as shown here. 

As with the pyrroles, N-chloroamides have been widely employed in indole chlorination [66JOC2627 80H( 14)867 81JOC2054]. Chloroindolen-ines may be isolated under controlled conditions [80H( 14)867 81JOC2054], 2-Phenyl-, l-methyl-2-phenyl-and 3-methyl-2-phenyl-indoles were converted by 1-chloroisatin (NCI) into the 3-chloro derivatives... 

Titanium powder (0.626 g, 13.07 mmol) is suspended in 10 mb DME. Me3SiCl 14 (1.59 mb, 13.07 mmol) and (iPrO)3TiCl (9 mol%) are added and the mixture heated under reflux for 68 h under argon. 2-AcetylbenzaniHde 2091 (ca. 4 mmol) is added to this preactivated titanium reagent and the mixture is heated under reflux for 2.5 h. After filtration and evaporation of the filtrate the residue is chromatographed with hexane-ethylacetate (20 1) on silica gel to give 3-methyl-2-phenyl-indole 2092 as colorless crystals, m.p. 91-93 °C, in 97% yield [64] (Scheme 13.31). 

Allen und Wilson 4) fiihrten die E. FiscHERsche Indolsynthese mit Phenylhydrazin durch, in dem der dem Benzolkern benachbarte Stickssoff einen UberschuB an 15N enthielt. Der gesamte UberschuB an 15N wurde im erhaltenen 2-Phenyl-indol gefunden, wie es nach der Theorie von Robinson und Robinson 171) und den Versuchen von E. Fischer 79) mit asymmetrischem Methylphenylhydrazin zu erwarten war. 

Keywords methyl phenyl ketone, 2-phenyl indole, formylation, Vilsmeier reagent, silica gel, microwave irradiation... 

The mechanism of melatonin s interaction with reactive species probably involves donation of an electron to form the melatoninyl cation radical or through a radical addition at the site C3. Other possibilities include hydrogen donation from the nitrogen atom or substitution at position C2, C4, and C7 and nitrosation [169]. The mechanisms by which melatonin protects against LP most likely involve direct or indirect antioxidant and free-radical scavenging activities of this indoleamine [169,171]. 2-Phenyl indole derivatives have redox properties because of the presence of an electron-rich aromatic ring system that allows the indoleamine to easily function as an electron donor. For these derivatives, the possible antioxidant mechanism might be most probably toward carbon-centered radicals described by Antosiewicz et al. [172]. 

The Fischer synthesis is the condensation of an aryl hydrazine with a ketone followed by cyclisation of the resultant hydrazone under acidic conditions to give the corresponding indole, as illustrated by the preparation of 2-phenyl indole 7.9. 

The quinolinium analogs of G32 and G49 were also prepared as control compounds, and neither of them showed any fluorescence change in the presence of GTP. Combined with the fact that none of the other 94 library members that originated from different aldehyde groups showed strong fluorescent response to GTP, we postulate that both the imidazonium and the 2-phenyl-indole moieties are important for selective GTP recognition. 

Thallation of benzanilides with thallium tris(trifluoroacetate) in a mixture of trifluoroacetic acid and ether gave the c rr/to-thallated products. Reaction of these products with copper(I) acetylide in acetonitrile led to the 2-benzamidotolanes (119), which were eventually elaborated into the 2-phenyl-indole derivatives. 111 ... 

Dimethylamino-methyl)-2-phenyl-indol 5 M > 3-Formyl-2-phenyl-indol 70-80% ... 

Jennings LD, Foreman KW, Rush TS et al (2004) Combinatorial synthesis of substituted 3-(2-indolyl)piperidines and 2-phenyl indoles as inhibitors of ZipA-FtsZ interaction. Bioorg Med Chem 12 5115-5131... 

A3-posilivc, DAPI-iicgalivc bands (Ambros and Sumner, 1987), which are the GC-richcsl bands of human chromosomes (DA PI is 4,6 diamino-2-phenyl indole). n situ hybridization of H3 isochore DNA established that T bands comprise GC-rich, gene-rich, single-copy DNA. Indeed Ihc contribution of rcpctilivc DNAs was suppressed by competition with excess unlabeled total human DNA and Alu sequences. The latter are the most abundant type of short interspersed elements, which have their highest density in the GC-richest isochorcs H2 and H3 (see Part 6). This also ruled out the possibility that T bands corresponded to GC-rich satellite DNAs, which was a distinct possibility until then. 

P-Indolebutyric acid Y-(lndole-3) butyric acid. See 3-lndolebutyric acid 1H-lndole-5,6-diol. See Dihydroxyindole IH-Indole, 2-phenyl- Indole, 2-phenyl-. See2-Phenylindole... 

Stabilizer C. See N,N -Diphenylthiourea Stabilizer l-FF. See 2-Phenyl indole Stabioi CA 580 i. See Calcium stearate Stabioi CA 1362. See Calcium behenate Stabioi CA 1733. See Calcium stearate Stabioi ZN 592 i. See Zinc stearate Stabioi ZN 1500. See Zinc 2-ethylhexanoate Stabiand . See Hydrogenated soybean oil Stabiec iDC 52, Stabiec iDC 85. See Lecithin Stabrom 909. See Bromine Stabyien 30. See Acrylates/vinyl isodecanoate crosspolymer... 

Lead carbonate basic Lead 2-ethylhexoate Lead phthalate, dibasic Lead stearate, dibasic Lead sulfate, basic Magnesium/aluminum/hydroxide/carbonate Methyltin tris (isooctylthioglycollate) Methyltin tris (2-mercaptoethyl oleate) p-Nonyl phenol (n-Octyl) tin S,S, S" tris (isooctyl mercaptoacetate) 2-Phenyl indole Thiodiglycol di-P-aminocrotonate Tris (nonyiphenyi) phosphite Tris (tridecyl) phosphite Zinc laurate Zinc stearate... 

Castro first documented cydoisomerization of ortho-alkynylanilines 96 to give the 2-phenyl indole 97 in the presence of substoidiiometric amounts of Cu(I) catalyst in excellent yield (Scheme 9.35) [77, 111]. Mechanistically, it is believed that 5-exo-dig cydization follows the generally accepted mechanism proposed for an intramolecular addition of various nucleophilic entities to transition metal-activated carbon-carbon multiple bonds. 

Reaction Procedure (Scheme 2.92) The Pd-loaded zeolite (0.125 mmol), lithium chloride (0.5 mmol), caesium carbonate (1 mmol), AT-acetyl 2-iodoaniline (0.5 mmol), phenyl acetylene (1.0 mmol), and DMF (10 ml) were added to a sealed tube. The reaction mixture was stirred for 6 h at 140 °C. The reaction mixture was diluted with saturated aqueous ammonium chloride. The product was isolated with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The reaction mixture was filtered and concentrated. The product was purified by silica gel column chromatography using hexane-ethyl acetate. 2-Phenyl indole was obtained as a pure product. 

CnHuClN Oa 6-Nitro-l, 3-diacetoxy-5.chlor acetoxy-2-phenyl-indol 21II140. 

Methyl-2-phenyl-indol 80, 474. 5-MoUiyl.2-pheDyl>mdol 80, 474. 

C3 5H2 9N3O, 2-Anilino-3-(1-methyl-2-phenyl-indol-3-yl)-3-phenyl-3H-indole monohydrate, 42B, 213... 

Kapuscinski, J. Skoczylas, B. Fluorescent complexes of DNA with DAPI (4, 6-diamidine-2-phenyl indole dihydrochloride) or DCI (4, 6-dicarboxyamide-2-phenyl indole). Nucleic Acids Res. 1978, 5, 3775-3799. 

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