Multicomponent Reactions with Cyclic Tertiary Amines Enabled by Facile C−N Bond Cleavage. Issue 18 (3rd April 2017)

• Record Type: Journal Article
• Authors: Zhu, Qiming; Yuan, Qinghe; Chen, Mingwei; Guo, Mengping; Huang, Hanmin
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 18(2017)
• Page Start: 5101
• Page End: 5105
• Publication Date: 2017-04-03
• Subjects: catalyst-free reactions -- C−N bonds -- C−S bonds -- multicomponent reaction -- tertiary amines; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201612017
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: A novel and catalyst‐free multicomponent reaction with cyclic tertiary amines, electron‐deficient aryl halides or heteroaromatic halides, and Na2 S enabled by facile C−N bond cleavage of the cyclic tertiary amines was developed. This direct and operationally simple method can be applied with a wide range of functional groups and provides an efficient and rapid approach to potentially drug‐like products containing amine, azaarene, thioether, or phenol ether functionalities in good to excellent yields. The utility of this method was demonstrated by the rapid synthesis of the analgesic ruzadolane. Abstract : All together now : A catalyst‐free multicomponent reaction with cyclic tertiary amines, electron‐deficient aryl halides or heteroaromatic halides, and Na2 S enabled by facile C−N bond cleavage of the cyclic tertiary amines was developed. This direct and operationally simple method shows good functional‐group tolerance and provides an efficient approach to drug‐like products containing amine, azaarene, thioether, or phenol ether functionalities.