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Synthesis via pummerer intermediates. II. . Disproportionation reactions of 3‐(methylsulfinyl)chromones and 3‐(methyl‐sulfinyl)quinolinones with hydrochloric acid
Author(s) -
Connor David T.,
von Strandtmann Maximillian
Publication year - 1978
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.5570150123
Subject(s) - chemistry , hydrochloric acid , disproportionation , pummerer rearrangement , medicinal chemistry , benzopyran , organic chemistry , catalysis , acetic anhydride
Sulfoxides ( 1 and 10 ) gave oxidation‐reduction products when treated with 5 N hydrochloric acid. 8‐Methoxy‐3‐(methylsulfinyl)‐4 H ‐benzopyran‐4‐one (1) gave 8‐methoxy‐3‐(methylthio)‐4 H ‐1‐benisopyran‐4‐one ( 4 ) and 8‐methoxy‐3‐(methylsulfonyl)‐4 H ‐1‐benzopyran‐4‐one ( 5 ), whereas 1‐melhyl‐3‐(methylsulfinyl)‐4(1 H )quinolinone ( 10 ) gave 1‐methyl‐3‐(methylthio)‐4(1 H )‐quinolinone ( 12 ) and 1‐methyl‐4(1 H )‐quinolinone ( 13 ).