3 ',4-dialkylthio-3,4 '-diquinolinyl sulfides with non-identical, alkyl groups

Authors
Nowak, M Pluta, K Szmielew, M Maslankiewicz, MJ Maslankiewicz, A
Citation
M. Nowak et al., 3 ',4-dialkylthio-3,4 '-diquinolinyl sulfides with non-identical, alkyl groups, HETEROCYCLE, 51(5), 1999, pp. 1109-1118
Citations number
19
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
51
Issue
5
Year of publication
1999
Pages
1109 - 1118
Database
ISI
SICI code
0385-5414(19990501)51:5<1109:3''SWN>2.0.ZU;2-J
Abstract
3',4-Dialkylthio-3,4'-diquinolinyl sulfides (6) were obtained by three meth ods in the reaction of thioquinanthrene (1) with sodium hydrosulfide follow ed by sequential S-alkylation of the 3- and 4-thiolate functions. Competiti ve S-alkylation of 3- and 4-quinolinethiolates (4) and (10) in DMSO showed three times greater susceptibility of the 3-thiolate function to the alkyla ting agent than the 4-thiolate function. 4-Quinolinethiolates (3) were conv erted into 4(1H)-quinolinethiones (8).