A convenient synthesis of 2-(F-alkyl)-4-hydroxyquinolines [1]

✍ Scribed by Huang Wei-Yuan; Liu Yan-Song; Lu Long

• Book ID: 104150691
• Publisher: Elsevier Science
• Year: 1994
• Tongue: English
• Weight: 673 KB
• Volume: 66
• Category: Article
• ISSN: 0022-1139
• DOI: 10.1016/s0022-1139(00)83977-9

✦ Synopsis

A convenient new route to 2-(F-alkyl)-4-hydroxyquinolines has been developed. In the presence of triethylamine, treatment of ethyl 2,2-dihydropolyfluoroalkanoates with aromatic amines in acetonitrile at 70 "C led to a mixture of the corresponding enamines and imines, which was cyclized in polyphosphoric acid (PPA) at 170 "C to give 2-(F-all@)-4-hydroxyquinolines in good yield. Yield (%)" Ratio of enaminesj iminesb CH3 CICFl CWFd3 CW% BrCF, -3 H CICFz Cl(CF-J2 Cl(CF& BrCF, Cl CVW3 CW% BrCF,