Synthesis of diverse di- to penta-substituted 1, 2-dihydropyridine derivatives from gold(I)-catalyzed intramolecular addition of tertiary enamides to alkynes. Issue 25 (17th June 2015)

• Record Type: Journal Article
• Authors: Zhang, Xingyi; Xu, Xin-Ming; Zhao, Liang; You, Jingsong; Zhu, Jieping; Wang, Mei-Xiang
• Is Part Of: Tetrahedron letters. Volume 56:Issue 25(2015)
• Page Start: 3898
• Page End: 3901
• Publication Date: 2015-06-17
• Subjects: Tertiary enamide -- 1, 2-Dihydropyridine -- Gold(I) catalysis -- Cyclization -- Pyridine; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.04.105
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: As 3-aza-1, 5-enynes, internal and terminal alkyne-bearing tertiary enamides underwent an efficient Au(I)-catalyzed 6- endo - dig cyclization reaction to afford a variety of di- to penta-substituted 1, 2-dihydropyridine derivatives in high yields. The cyclization proceeds through a cascade comprising an intramolecular nucleophilic addition of enaminic carbon to alkyne–gold(I) complex, deprotonation, and protodeauration steps. Au(I)-catalyzed tertiary enamide–alkyne cyclization coupled with consecutive oxidative aromatization provided a straightforward route to polysubstituted pyridines.