TY - JOUR A1 - Schmidt, Bernd A1 - Elizarov, Nelli A1 - Berger, René A1 - Petersen, Monib H. T1 - From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction JF - Synthesis N2 - 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. KW - acetanilides KW - deacetylation KW - diazonium salts KW - palladium KW - Matsuda-Heck reaction Y1 - 2013 U6 - https://doi.org/10.1055/s-0032-1316874 SN - 0039-7881 VL - 45 IS - 9 SP - 1174 EP - 1180 PB - Thieme CY - Stuttgart ER -