【Tetrahedron 1995, 51, 12869】
反應(yīng)操作：?；桨罚? mol. equiv.）和Vilsmeier試劑{由POC13 (7 mol. equiv.) 和N,N-dimethylformamide (DMF, 2.5 mol. equiv.) 制備得到}在75℃反應(yīng)4-20小時(shí)就可得到喹啉產(chǎn)物。反應(yīng)完畢倒入冰水中，過濾即可得到產(chǎn)物，個(gè)別產(chǎn)物需要堿化后過濾。活化的芳胺底物 [e.g. R = 4-Me (70%), 4-OMe (56%)] 反應(yīng)較快產(chǎn)率相對較高，鈍化的芳胺產(chǎn)率較低[e.g. R = 4-Br (23%), 4-C1 (2%), 4-NO2 (O%)] 。
反應(yīng)機(jī)理
反應(yīng)實(shí)例
2-chloro-3-quinolinearboxaldehyde (34) To an ice-cooled solution of N,N-dimethylformamide (10.95 g, 11.6 mL, 0.15 mol) was added dropwise with stirring phosphoryl chloride (53.7 g, 32.3 mL, 0.35 mol). Acetanilide 33 (6.75 g, 0.05 mol) was then added and the reaction raised to 75 ℃ and stirred for a further 16.5 h. The reaction mixture was poured into ice-water (300 mL) and stirred for 0.5 h at < 10 ℃. The precipitated solid was collected by filtration and washed well with water (100 mL), air dned and recrystallised from ethyl acetate to afford the product 34 (6.5 g, 68%) as a white solid, mp 148 - 149 ℃; 'H NMR (a-DMSO) 6 7.60 - 8.30 (m, 4H), 8.83 (s, lH), 10.35 (s, 1H).
【.J. Chem. Soc., Perkin Trans. 1 1981, 1520】
【Synlett 2001, 251】
【J. Chem. SOC., Perkin Trans. 1 1981, 1531】
【Tetrahedron Lett. 1980, 21, 3721】
【J. Org. Chem. 2000，65，7110】
【Bioorg. Med. Chem. Lett. 1996, 6, 1635】
編譯自：Name Reactions in Heterocyclic Chemistry，Jie-Jack Li，443-449
