Studies on the [2+3] cycloaddition reaction of nitrile oxides to abietic acid esters

[2+3] Dipolar cycloadditions of aromatic nitrile oxides to abietic acid esters were investigated. The reactions showed complete site selectivity and regioselectivity, while the stereoselectivity depended on the structures of the dipolarophiles.

Oxidant-controlled divergent transformations of 3-aminoindazoles for the synthesis of pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals

An oxidant-controlled divergent reactivity of 3-aminoindazoles is presented, which enables the [3 + 3] annulation and C–H arylation of ketene dithioacetals in disparate pathways to assemble pyrimido[1,2-b]-indazoles and aromatic nitrile-derived dithioacetals.

One-pot synthesis of 4′-alkyl-4-cyanobiaryls on the basis of the terephthalonitrile dianion and neutral aromatic nitrile cross-coupling

A convenient one-pot approach to alkylcyanobiaryls is described. The method is based on biaryl cross-coupling between the sodium salt of the terephthalonitrile dianion and a neutral aromatic nitrile in liquid ammonia, and successive alkylation of the long-lived anionic intermediate with alkyl bromides. The reaction is compatible with benzonitriles that contain methyl, methoxy and phenyl groups, fluorine atoms, and a 1-cyanonaphthalene residue. The variety of ω-substituted alkyl bromides, including an extra bromine atom, a double bond, cyano and ester groups, as well as a 1,3-dioxane fragment are suitable as alkylation reagents.