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Homolytic alkylation of some 3,4‐quinolinediyl bis‐sulfides under minisci reaction conditions
Author(s) -
Maślankiewicz Andrzej,
Michalik Ewa,
Ciunik Zbigniew
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.5570450235
Subject(s) - chemistry , homolysis , isopropyl , alkylation , medicinal chemistry , sodium methoxide , alkyl , radical , methyl iodide , hydrogen peroxide , ring (chemistry) , organic chemistry , methanol , catalysis
Reaction of hydrogen sulfate of 3,4‐quinolinediyl bis‐sulfides 1a , 2a , 3a , and 4a with isopropyl and cyclohexyl radicals formed from alkyl iodide/hydrogen peroxide/DMSO/Fe ++ salt system took place at α‐quinolinyl position and led to the respective mono‐ and dialkyl derivatives 1b‐e , 2b‐e , 3b,c , and 4b,c . Action of sodium methoxide towards isopropyl derivatives 1b,c and 2b,c caused the 1,4‐dithiin ring opening to form (after S ‐methylation) derivatives of 3,4′‐ and 3,3′‐diquinolinyl sulfides 6a,b and 7a,b .