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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.
Author details: | Bernd SchmidtORCiDGND, Nelli Elizarov, René BergerGND, Monib H. Petersen |
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DOI: | https://doi.org/10.1055/s-0032-1316874 |
ISSN: | 0039-7881 |
Title of parent work (English): | Synthesis |
Publisher: | Thieme |
Place of publishing: | Stuttgart |
Publication type: | Article |
Language: | English |
Year of first publication: | 2013 |
Publication year: | 2013 |
Release date: | 2017/03/26 |
Tag: | Matsuda-Heck reaction; acetanilides; deacetylation; diazonium salts; palladium |
Volume: | 45 |
Issue: | 9 |
Number of pages: | 7 |
First page: | 1174 |
Last Page: | 1180 |
Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie |
Peer review: | Referiert |