Synthesis of α,β-Unsaturated 2-Oxopyrrolidinyl Acetamide Derivatives by Application of the Ugi/RCM Reaction Sequence

Title
Synthesis of α,β-Unsaturated 2-Oxopyrrolidinyl Acetamide Derivatives by Application of the Ugi/RCM Reaction Sequence
Authors
구일회강순방금교창김유승
Keywords
Ugi reaction; Multicomponent reaction; Piracetam; Nootropics; Lactam
Issue Date
2011-08
Publisher
Bulletin of the Korean Chemical Society
Citation
VOL 32, NO 8, 3167-3170
Abstract
The Ugi four-component condensation reaction have been widely used for the construction of focused library and diversity-oriented approach especially in the drug discovery, and also applied to introduce more complexity by utilizing bifunctional components or post transformations.1 The various constructions of γ-lactam ring based on the Ugi reaction have been reported. The preparations were successfully accomplished by using γ-ketoacids as bifunctional starting materials2 or post transformation strategies such as Horner-Wadsworth-Emmons reaction,3 Heck reaction,4 cyclization, 5 deBoc-Cyclization,6 and radical cyclization7 from appropriate starting materials. It was also found that bicyclic γ-lactam moiety can be accessed by a tandem Ugi/Diels– Alder reaction followed by domino metathesis.8 The sequential Ugi reaction/ring-closing metathesis (RCM) reaction provided powerful synthetic tools toward macrocyclic lactams larger than five-membered 2-pyrrolidones.
URI
http://pubs.kist.re.kr/handle/201004/45647
ISSN
0253-2964
Appears in Collections:
KIST Publication > Article
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