Indolyl 3 acetonitrile

Several (7-aza-3-indolyl)acetonitriles were prepared by various methods including treatment of the azaindole in DMF with sodium hydride followed by chloroacetonitrile. Also, 4-, 5-, 6-, and 7-azaindoles gave the corresponding 2- and 3-indolyl-j3-propionitriles when heated with acrylonitrile. 

As mentioned above, (7-aza-3-indolyl)acetonitrile (129) was reduced catalytically to give 7-azatr3rptamine (131). Other 7-azatryptamines prepared similarly are 1-methyl, 1-benzyl, 2-methyl, and l-(2-aminoethyl). This patent also describes several other 1-, 2-, and 3-(aminoalkyl) derivatives of the four azaindole isomers. The several 4-, 5-, 6-, and 7-azaindolylalkanonitriles were also treated with hydrolylamine to give amidoximes and with hydrogen chloride in chloroform, followed by ammonia to give amidines. ... 

In 1925 Majima and Hoshino reported the formation of 3-indolyl-acetonitrile (229) by the action of chloroacetonitrile on indole magnesium iodide in anisolc.100 2-Methyl-3-indolylacetonitrile (230) was obtained by the action of chloroacetonitrile on 2-methylindole magnesium iodide in ether.37... 

Recently the use of the boron trifluoride catalysed reaction in the synthesis of the oxazolylindole fragment 25 of the natural product diazonamide A has been reported.<96SL609> Thus the BF3-mediated reaction of the indolyl diazoketoester with acetonitrile gave oxazole 25 with simultaneous removal of the Boc-protecting group (Scheme... 

Cyan-indolyl-(3)-acetonitril, by E. Hardegger and H. Corrodi, Helv. Chim. Acta, 39 (1956) 984-986. 

In 2006, Xu and Xia et al. revealed the catalytic activity of commercially available D-camphorsulfonic acid (CS A) in the enantioselective Michael-type Friedel-Crafts addition of indoles 29 to chalcones 180 attaining moderate enantiomeric excess (75-96%, 0-37% ee) for the corresponding p-indolyl ketones 181 (Scheme 76) [95], This constitutes the first report on the stereoselectivity of o-CSA-mediated transformations. In the course of their studies, the authors discovered a synergistic effect between the ionic liquid BmimBr (l-butyl-3-methyl-l/f-imidazohum bromide) and d-CSA. For a range of indoles 29 and chalcone derivatives 180, the preformed BmimBr-CSA complex (24 mol%) gave improved asymmetric induction compared to d-CSA (5 mol%) alone, along with similar or slightly better yields of P-indolyl ketones 181 (74-96%, 13-58% ee). The authors attribute the beneficial effect of the BmimBr-D-CSA combination to the catalytic Lewis acid activation of Brpnsted acids (LBA). Notably, the direct addition of BmimBr to the reaction mixture of indole, chalcone, d-CSA in acetonitrile did not influence the catalytic efficiency. 

Recently, evidence for the transient ex istence of cation-radicals from simple pyrroles and indoles has been furnished by the observation of anodic regiospecific cyanation of these heterocycles.455 Both heterocycles are preferentially cyanated at the 2-position. Methyl side chains at these positions are also activated to cyanation and deuteration. Indole cation-radicals have been generated by photoionization in an aqueous medium.456 Unsubstituted at N, their lifetime in neutral solution is 10-6sec before they lose the N-proton however, it is longer in more acidic conditions.456 The photophysical properties of indole, its cation-radical, and neutral radical have been the subject of a recent theoretical analysis.457 On anodic oxidation of 2,3-diphenyl indole in acetonitrile, the initially formed cation-radicals dimerize to a product identified, primarily on the basis of 13C NMR, as 3-(5-indolyl)-indolenine (141).458... 

Dehaen et al. [100,101] found another interesting way to synthesize the IC backbone. They first used a condensation of indole and aldehyde in the presence of iodine in acetonitrile to afford 3,3,-bis(indolyl)mclhanc. The IC moiety was obtained by treating the previous compound with triethyl orthoformate and a catalytic amount of a strong acid (sulfuric acid or methanesulfonic... 

However, aryl cyanides are more directly obtained by reaction of the arylthallium compound with various copper cyanides. Different reaction systems have been reported, such as CuCN or Cu(CN)2 in acetonitrile or pyridine with arylthallium acetate perchlorate monohydrates. Other systems involve the arylthallium bistrifluoroacetate with CuCN in acetonitrileor in DMF. With these systems, a number of aryl cyanides (114), heteroaryl cyanides (115) 25,126 indolyl cyanides (116) and (117)124 148 have been prepared. 

Indolyl-(3)-methyl]- 1,6-diphenyl-tetrahydroimidazol Die Mischung von 22,5 g Indolyl-(3)-acetonitril, 40 g 1,2-Dianilino-athan. 240 ml Methanol und 10 m/ Eisessig wird in Gegenwart von 22 g Raney-Nickel bci 40° und 110 bar Wasserstoff hydriert. Nach der Aufnahme von einem Molaquivalent Wasserstoff wird der Autoklaveninhalt filtriert und der Nickel-Riickstand mehrmals mit Methanol und Benzol ausgckocht. 

The enzyme systems of single plant species differ specifically from one another thus, the conversion of the precursor molecules will also be specific in them. For example, indolyl-3-acetonitrile shows strong activity on wheat and oat (Bentley and Housley, 1952), while it is inactive in the pea test (Seeley et al.. 1956). 

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