A New Synthetic Route to Aliphatic and Alicyclic Nitriles via Homolytic Desulfurization of α-(Dithiocarbamoylthio) Nitriles

Ruthenium-catalyzed intramolecular selective halogenation of O-methylbenzohydroximoyl halides: a new route to halogenated aromatic nitriles.

The intramolecular halogenation of O-methylbenzohydroximoyl halides in the presence of a Ru catalyst and the ligand diphenylacetylene afforded halo substituted aromatic nitriles in a highly regioselective manner. Further, substituted nitriles were converted into substituted tetrazole derivatives in the presence of NaN3 and I2.

Catalytic asymmetric synthesis of secondary nitriles via stereoconvergent Negishi arylations and alkenylations of racemic α-bromonitriles.

The first method for the stereoconvergent cross-coupling of racemic α-halonitriles is described, specifically, nickel-catalyzed Negishi arylations and alkenylations that furnish an array of enantioenriched α-arylnitriles and allylic nitriles, respectively. Noteworthy features of this investigation include: the highly enantioselective synthesis of α-alkyl-α-aryl nitriles that bear secondary α-al...

arylaminotetrazoles : via [2+3] cycloaddition of nitriles and sodium azide via solid acid catalysis

The [3+2] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of zeolite and sulfated Zircona as effective catalyst and in the water and DMF/MeOH, to give the corresponding arylaminotetrazoles in good to high yields. The reaction most probably precedes through the in situ formation of a catalyst azide species, followed by a successive [3+2] cycloaddition wi...

Trimereation of Aromatic Nitriles

Polyfunctional nitriles in organic syntheses: a novel route to aminopyrroles, pyridazines and pyrazolo[3,4-c]pyridazines.

Phenacylmalononitrile 1 reacts with dimethylformamide dimethyl acetal to yield an enaminone which could be readily converted into a pyrrole or an aminopyridazine by treating with ammonium acetate and hydrazine hydrate, respectively. Compound 1 reacted with hydrazine hydrate in ethanol at room temperature to yield the dihydropyridazine 9 as a single product. In refluxing ethanol this product fur...