Ring-Closing Metathesis of Ene-Ynamide: Application to the Synthesis of Medium-Sized Cyclic Dienamide

Ring-closing metathesis (RCM) of ene-ynamide, which could be applied to the synthesis of various heterocycles containing 7- and 8-membered rings, was investigated. Ene-ynamides are easily synthesized by the known method. When a toluene solution of ene-ynamide was stirred in the presence of a catalyt...

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Bibliographic Details
Published in:Macromolecular symposia. 2010-07, Vol.293 (1), p.5-9
Main Authors: Wakamatsu, Hideaki, Sakagami, Maiko, Hanata, Miyuki, Takeshita, Mitsuhiro, Mori, Miwako
Format: Article
Language:English
Subjects:
Decomposition reactions
Ethylene
Heterocyclic compounds
medium-sized heterocycles
Metathesis
RCM
ring-closing metathesis
Ruthenium
Synthesis
Toluene
ynamide
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Summary:Ring-closing metathesis (RCM) of ene-ynamide, which could be applied to the synthesis of various heterocycles containing 7- and 8-membered rings, was investigated. Ene-ynamides are easily synthesized by the known method. When a toluene solution of ene-ynamide was stirred in the presence of a catalytic amount of second-generation ruthenium carbene complex 1 under an ethylene atmosphere, RCM proceeded smoothly to provide a heterocyclic compound having a diene moiety in good to high yield. A substituent of the ynamide moiety affected the yield of the cyclized product.
ISSN:1022-1360
1521-3900
1521-3900
DOI:10.1002/masy.200900035