Studies on heterocyclic chemistry. Part XV. Synthesis of phosphine N-styrylimides by the reaction of 2H-azirines with triphenylphosphine and a tetrahalogenomethane, and their transformation into isoquinoline derivatives

Abstract

Phosphine N-styrylimides are prepared by the ring-opening of 2,3-diaryl-2H-azirine-2-carboxamides or 2-alkoxy-carbonyl-3-aryl-2H-azirines with a combination of triphenylphosphine and a tetrahalogenomethane; mechanisms for the reaction are discussed. Phosphine N-(β-cyano-β-arylstyryl)imides afford 3-aryl-1-arylamino-4-cyano-isoquinolines when treated with aryl isocyanates.