Me3SiCl-promoted three-component coupling reaction of a functionalized enamine, an acetal, and an alkyne: an unprecedented approach to the synthesis of tetrasubstituted pyridines via a [3 + 2 + 1] intermolecular cyclization.
We have identified a Me3SiCl-mediated three-component coupling reaction of a functionalized enamine, N,N-dimethylformamide diethyl acetal, and an internal alkyne having an electron-withdrawing group that produces 2,3,4,5-tetrasubstituted pyridine derivatives in good to excellent yields via a single-step reaction.
Sasada
Toshiaki
T
Department of Pure and Applied Chemistry, Faculty of Science and Technology, Tokyo University of Science (RIKADAI), Noda, Chiba 278-8510, Japan.
Sakai
Norio
N
Konakahara
Takeo
T
D000080:Acetals / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D004126:Dimethylformamide; D005559:Formamides / Q000737:chemistry*; D008956:Models, Chemical; D011725:Pyridines / Q000138:chemical synthesis*; D014297:Trimethylsilyl Compounds / Q000737:chemistry*
D000080:Acetals; D000480:Alkynes; D000588:Amines; D005559:Formamides; D011725:Pyridines; D014297:Trimethylsilyl Compounds; D004126:Dimethylformamide