Synthesis of 4-(<i>tert</i>-Butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine
Rasma Kroņkalne,
Rūdolfs Beļaunieks,
Māris Turks
Affiliations
Rasma Kroņkalne
Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia
Rūdolfs Beļaunieks
Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia
Māris Turks
Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, LV-1048 Riga, Latvia
SN2 rection between 4-(tert-butyldimethylsilyl)hex-5-yn-1-yl 4-methylbenzenesulfonate and NaN3 in DMF at 80 °C provided (6-azidohex-1-yn-3-yl)(tert-butyl)dimethylsilane intermediate, which underwent in situ intramolecular thermal Huisgen azide–alkyne cycloaddition reaction. This one-pot process gave 4-(tert-butyldimethylsilyl)-4,5,6,7-tetrahydro-[1,2,3]triazolo[1,5-a]pyridine in 78% yield.
