Premium
Synthesis of 8‐hydroxyquinolines with amino and thioalkyl functionalities at position 4
Author(s) -
Omar Walaa A. E.,
Heiskanen Juha P.,
Hormi Osmo E. O.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450247
Subject(s) - chemistry , nucleophile , pyrrolidine , yield (engineering) , chlorine , tosyl , sulfur , position (finance) , chlorine atom , nitrogen , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , materials science , finance , economics , metallurgy
ix 8‐hydroxyquinolines with amino and thioalkyl functionalities at position 4 have been prepared. The synthesis starts with chlorination of the readily available 4‐hydroxy‐8‐tosyloxyquinoline to give 4‐chloro‐8‐tosyloxyquinoline in 94% yield. Treatment of the 4‐chloro‐8‐tosyloxyquinoline with sulphur and nitrogen nucleophiles produces the target 4‐amino and 4‐thioalkyl‐8‐hydroxyquinolines in more than 70% yield. In case of sulphur nucleophiles and pyrrolidine, the removal of the protecting tosyl group at position 8 occurs simultaneously with the substitution of chlorine at position 4.