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From paracetamol to rolipram and derivatives - application of deacetylation-diazotation sequences and palladium-catalyzed matsuda-heck reaction

  • 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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Metadaten
Author:Bernd SchmidtORCiDGND, Nelli Elizarov, Rene Berger, Monib H. Petersen
DOI:https://doi.org/10.1055/s-0032-1316874
ISSN:0039-7881 (print)
Parent Title (English):Synthesis
Publisher:Thieme
Place of publication:Stuttgart
Document Type:Article
Language:English
Year of first Publication:2013
Year of Completion:2013
Release Date:2017/03/26
Tag:Matsuda-Heck reaction; acetanilides; deacetylation; diazonium salts; palladium
Volume:45
Issue:9
Pagenumber:7
First Page:1174
Last Page:1180
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Peer Review:Referiert