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Synthesis of 2‐(4‐Quinolyl) and 2‐(3‐Quinolyl) Chromone Derivatives
Author(s) -
Hsu KuangKann,
Sun ShaoWen,
Chen YuehHung
Publication year - 1982
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198200005
Subject(s) - chemistry , chromone , dehydrogenation , yield (engineering) , organic chemistry , medicinal chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
In continuing search of the structure‐activity relationship of heterocyclic chromones, 4‐quinolyl and 3‐quinolyl moieties were each introduced to the C‐2 position of chromones. A total of 12 quinolyl chromones were synthesized. 4‐Quinolinecarboxaldehyde was condensed with 2‐hydroxyacetophenones to provide the chalcones. These intermediates were then subjected to selenium dioxide dehydrogenation to yield the 6 new 4‐quinolyl chromones. 3‐Quinolinecarboxaldehyde was condensed with 2‐hydroxyacetophenones in the presence of dilute alkali to give aldol compounds of chalcones (dehydration products of aldols). Ring cyclization of the chalcones yielded the other 6 new 3‐quinolyl chromones.