Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 9, Pages 1174-1180Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1316874
Keywords
acetanilides; deacetylation; diazonium salts; palladium; Matsuda-Heck reaction
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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.
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