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Synthesis 2013; 45(9): 1174-1180
DOI: 10.1055/s-0032-1316874
DOI: 10.1055/s-0032-1316874
paper
From Paracetamol to Rolipram and Derivatives: Application of Deacetylation–Diazotation Sequences and Palladium-Catalyzed Matsuda–Heck Reaction
Further Information
Publication History
Received: 30 January 2013
Accepted after revision: 01 March 2013
Publication Date:
14 March 2013 (online)
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.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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