Solvent-Free Multicomponent Reactions for the Synthesis of Tetrahydroquinolines Catalyzed by Lewis Acid

• Main Authors: Chueh Lee, 李爵
• Other Authors: David Woei-Ming Liang
• Format: Others
• Language: zh-TW
• Published: 2008
• Online Access: http://ndltd.ncl.edu.tw/handle/57905531007611082460

碩士 === 靜宜大學 === 應用化學研究所 === 96 === Tetrahydroquinolines derivatives 2 and 3 have been synthesized via aza Diels–Alder reaction of aryl imines formed in situ from aniline and arylaldehydes 1, with cyclic enol ethers, such as 2,3-dihydrofuran (DHF) and 3,4-dihydro-2H-pyran (DHP), catalyzed by using 10 mol % of trifluoroacetic acid (TFA) under solvent-free conditions at room temperature in good yields. Readily prepared Lewis acid solid supporting materials, such as FeCl3-SiO2 and HClO4-SiO2 were also employed to aza Diels–Alder reaction to give tetrahydroquinolines derivatives 2 and 3. According to the principles of green chemistry, solid-supported material of FeCl3-SiO2 and HClO4-SiO2 can be recovered easily and reused efficiently.