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

Bernd Schmidt; Nelli Elizarov; René Berger; Monib H. Petersen

doi:10.1055/s-0032-1316874

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(9): 1174-1180
DOI: 10.1055/s-0032-1316874

paper

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

Bernd Schmidt*

Universität Potsdam, Institut für Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24–25, 14476 Potsdam-Golm, Germany Fax: +49(331)9775059 eMail: bernd.schmidt@uni-potsdam.de

,

Nelli Elizarov

Universität Potsdam, Institut für Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24–25, 14476 Potsdam-Golm, Germany Fax: +49(331)9775059 eMail: bernd.schmidt@uni-potsdam.de

,

René Berger

Universität Potsdam, Institut für Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24–25, 14476 Potsdam-Golm, Germany Fax: +49(331)9775059 eMail: bernd.schmidt@uni-potsdam.de

,

Monib H. Petersen

Universität Potsdam, Institut für Chemie (Organische Synthesechemie), Karl-Liebknecht-Straße 24–25, 14476 Potsdam-Golm, Germany Fax: +49(331)9775059 eMail: bernd.schmidt@uni-potsdam.de

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Abstract

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Abstract

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.

Key words

acetanilides - deacetylation - diazonium salts - palladium - Matsuda–Heck reaction

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Referenzen

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