Synthesis of 4-alkoxy-8-hydroxyquinolines.
Quinolines with a hydroxyl group at the 8-position and an alkoxy group at the 4-position are rare compounds. In this paper the synthesis of five 4-alkoxy-8-hydroxyquinolines is reported. The key reaction in the synthetic route is a selective protection of the hydroxyl group at C-atom 8 in 4,8-dihydroxyquinoline with a tosyl group and the hydrolytic removal of the protective group after the alkylation. The tosyl group is stable during the alkylations with various alkylating agents in the presence of sodium hydride.
Heiskanen
Juha P
JP
Department of Chemistry, University of Oulu, P.O. Box 3000, 90014 Oulu, Finland.
Omar
Walaa A E
WA
Ylikunnari
Mari K
MK
Haavisto
Kirsi M
KM
Juan
Maria J
MJ
Hormi
Osmo E O
OE