4.5 Article

From Paracetamol to Rolipram and Derivatives: Application of Deacetylation-Diazotation Sequences and Palladium-Catalyzed Matsuda-Heck Reaction

Journal

SYNTHESIS-STUTTGART
Volume 45, Issue 9, Pages 1174-1180

Publisher

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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