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Oligomers with four 3,4‐quinolinediyl units and α,ω‐bis (4‐chloro‐3‐quinolinylthio)alkanes
Author(s) -
Boryczka Stanislaw,
Rudnik Magdalena,
Maślankiewicz Andrzej
Publication year - 1996
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.5570330125
Subject(s) - chemistry , sodium methoxide , hydrolysis , phosphoryl chloride , boiling , chloride , sodium , medicinal chemistry , methoxide , methanol , organic chemistry
Starting from the reaction of thioquinanthrene 1 with sodium methoxide followed by the reaction with α,ω‐dihalogenoalkanes, title bis‐methoxy oligomers 4a‐c with four 3,4‐quinolinediyl units were prepared (40–91%). Acid catalysed hydrolysis of methoxy groups in 4a‐c gave tetramers 5a‐c (46–94%) with two 4(1 H )‐quinolinone functions. The reactions of bis‐quinolinones 5a‐c with phosphoryl chloride in DMF run as deoxo‐chlorination and afforded tide dichlorotetramers 6a‐c (51–66%) with 4‐chloroquinolinyl groups. The treatment of bis‐methoxy tetramers 4a ‐c with boiling phosphoryl chloride led to title α,ω‐bis(4‐chloro‐3‐quinolinylthio)alkanes 7a‐c (52–56%) and thioquinanthrene (65–70%).