High-yielding synthesis of Nefopam analogues (functionalized benzoxazocines) by sequential one-pot cascade operations

An efficient amine-/ruthenium-catalyzed three-step process for the synthesis of Nefopam analogues was achieved through combinations of cascade enamine amination/iso-aromatization/allylation and diene or enyne metathesis as key steps starting from functionalized Hagemann's esters. In this commun...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2009-01, Vol.7 (17), p.3372-3378
Main Authors: Ramachary, Dhevalapally B, Narayana, Vidadala V, Prasad, M Shiva, Ramakumar, Kinthada
Format: Article
Language:English
Subjects:
Alkenes - chemistry
Amines - chemistry
Benzoxazoles - chemistry
Catalysis
Nefopam - analogs & derivatives
Nefopam - chemical synthesis
Organic Chemistry Phenomena
Ruthenium
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Summary:An efficient amine-/ruthenium-catalyzed three-step process for the synthesis of Nefopam analogues was achieved through combinations of cascade enamine amination/iso-aromatization/allylation and diene or enyne metathesis as key steps starting from functionalized Hagemann's esters. In this communication, we discovered the application of ruthenium-catalysis on olefins containing free amines without in situ formation of salts.
ISSN:1477-0520
1477-0539
DOI:10.1039/b910397j