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/isoaromatization/allylation and diene or enynemetathesis as key steps starting from functionalized Hagemann's esters. In this communic...

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Published inOrganic & biomolecular chemistry Vol. 7; no. 17; pp. 3372 - 3378
Main Authors Ramachary, Dhevalapally B., Narayana, Vidadala V., Prasad, M. Shiva, Ramakumar, Kinthada
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 01.01.2009
Subjects
Alkenes - chemistry
Amines - chemistry
Benzoxazoles - chemistry
Catalysis
Chemistry
Chemistry, Organic
Nefopam - analogs & derivatives
Nefopam - chemical synthesis
Organic Chemistry Phenomena
Physical Sciences
Ruthenium
Science & Technology
ORGANOCATALYTIC MULTICOMPONENT REACTIONS
ORGANO-CLICK REACTIONS
ASYMMETRIC-SYNTHESIS
RING-CLOSING METATHESIS
7-MEMBERED RINGS
PULL DIENAMINE PLATFORM
ACID-CATALYZED CASCADE
OLEFIN METATHESIS
STEREOSELECTIVE-SYNTHESIS
NK1 ANTAGONISTS
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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/isoaromatization/allylation and diene or enynemetathesis 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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1477-0520
1477-0539
DOI:10.1039/b910397j