反応 #1104820

反応方程式

ammonium chloride

n-Butyllithium

methyl 2-cyanomethylbenzoate

phenyl azide

citric acid

→

3-phenyl-1,2,3-triazolo[4,5-c]isoquinolin-5-one

収率 64.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe green solution was stirred at −78° C. for 1.5 h
2. 2
   温度then warmed to r.t. over 30 min
3. 3
   その他The white precipitate was collected
4. 4
   洗浄washed with water and diethyl ether
5. 5
   その他dried

実験手順

n-Butyllithium (1.6 M, 7.5 ml, 12 mmol) was added dropwise at −78° C. over 5 min to a stirred solution of methyl 2-cyanomethylbenzoate (Tetrahedron Lett., 1991, 32, 4133-4134) (2.10 g, 12 mmol) in dry THF (50 ml) under nitrogen. The deep red solution was stirred at −78° C. for 10 min, followed by the addition of a solution of phenyl azide (1.47 g, 12.3 mmol) in dry THF (10 ml). The green solution was stirred at −78° C. for 1.5 h then warmed to r.t. over 30 min, becoming bright blue. Saturated aqueous ammonium chloride (50 ml) was added and the mixture was acidified to pH 5 with 1M citric acid. The white precipitate was collected and washed with water and diethyl ether, then dried to give 3-phenyl-1,2,3-triazolo[4,5-c]isoquinolin-5-one (2.00 g, 64%). δH (360 MHz; DMSO) 7.58-7.68 (4H, m), 7.80-7.84 (2H, m), 7.93 (1H, ddd, J=8, 8 and 1), 8.30 (2H, d, J=8) and 12.80 (1H, s); m/z (ES+) 263 (M+H+).

出典