A novel atom-economic synthesis of functionalized imidazolidines through copper(I)-catalyzed domino three-component coupling and cyclization reactions

An interesting approach to functionalized imidazolidines is described. These compounds are obtained in a copper(I)-catalyzed domino three-component coupling and cyclization reaction involving two formaldehyde-derived imine units and a terminal alkyne. Alternatively, imidazolidines can be obtained fr...

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Bibliographic Details
Published inTetrahedron Vol. 70; no. 19; pp. 3134 - 3140
Main Authors Li, Yufeng, Wu, Zhengguang, Shi, Jie, Bu, Hongzhong, Gu, Jiachao, Pan, Yi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 13.05.2014
Elsevier
Subjects
Alkynes
Chemistry
Chemistry, Organic
Construction materials
Coupling (molecular)
Cyclization
Imines
Multicomponent reactions
Nitrogen heterocycles
Physical Sciences
Science & Technology
Strategy
Synthesis (chemistry)
Terminals
Tetrahedrons
Multicomponent reactions
Cyclization
Imines
Nitrogen heterocycles
Alkynes
NITROGEN-HETEROCYCLES
ENANTIOSELECTIVE SYNTHESIS
RING
2-PYRIDINECARBOXALDEHYDE
PROPARGYLAMINES
N-HETEROCYCLIC CARBENES
DERIVATIVES
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Summary:An interesting approach to functionalized imidazolidines is described. These compounds are obtained in a copper(I)-catalyzed domino three-component coupling and cyclization reaction involving two formaldehyde-derived imine units and a terminal alkyne. Alternatively, imidazolidines can be obtained from propargylamines and formaldehyde-derived imines. This strategy provides a straightforward and atom-economic pathway to construct imidazolidines with high yields and benefits from readily available starting materials, convenient one-pot operations. [Display omitted]
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2014.03.063