A mechanistic insight into the chemoselectivity of the reaction between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids

Reactions between 3-phenyl-2-propynenitrile, secondary phosphine oxides and pyridinoids have been implemented and studied. Pyridine and isoquinoline react with propynenitrile and phosphine oxides at room temperature according to the N-vinylation/C-phosphorylation scheme to afford (Z)-N-(2-cyano-1-phenyl)ethenylphosphoryl-1,4dihydropyridines or -1,2-dihydroiso quinolines. In the case of pyridine on heating (80-85 degrees C), the reaction gives 4-phosphorylpyridines (SNHAr reaction) and 3-phenylacrylonitrile oligomers.

Automated summary

Reactions between 3-phenyl-2-propynenitrile, secondary phosphine oxides, and pyridinoids have been studied, resulting in the formation of different products and reaction mechanisms under different conditions.