From paracetamol to rolipram and derivatives: Application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction

摘要

A six-step synthesis of the antidepressant rolipram from the popular analgetic 4-acetamidophenol (paracetamol) is described. The steps include oxidative functionalization of the aromatic core, diazonium salt formation via deacetylation-diazotation, Matsuda-Heck reaction, conjugate addition of nitromethane, and hydrogenative cyclization.