A novel redox reaction between 8-Aza-5,7-dimethyl-2-trifluoromethylchromone and alkyl mercaptoacetates. Facile synthesis of CF3-containing 2-pyridone derivatives.
8-Aza-5,7-dimethyl-2-trifluoromethylchromone reacts with alkyl mercaptoacetates in the presence of triethylamine to give pyrido derivatives of 2-oxa-7-thiabicyclo[3.2.1]octane, which undergo the reductive ring opening to alkyl 2-[[3-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-3-oxo-1-(trifluoromethyl)propyl]sulfanyl]acetates. The latter can be also obtained directly from 8-aza-5,7-dimethyl-2-trifluoromethylchromone and behave as the masked alpha,beta-unsaturated ketone, 4,6-dimethyl-3-(4,4,4-trifluorobut-2-enoyl)pyridin-2(1H)-one. This compound was independently synthesized from 3-acetyl-4,6-dimethyl-2-pyridone, and its synthetic potential was studied. A wide variety of 2-pyridone derivatives containing the CF(3) group have been prepared in good to moderate yields.
Sosnovskikh
Vyacheslav Ya
VY
Department of Chemistry, Ural State University, Lenina 51, 620083 Ekaterinburg, Russia. vyacheslav.sosnovskikh@usu.ru
Barabanov
Mikhail A
MA
Usachev
Boris I
BI
D000085:Acetates / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D002867:Chromones / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry*; D010084:Oxidation-Reduction; D011728:Pyridones / Q000138:chemical synthesis*; D013438:Sulfhydryl Compounds / Q000737:chemistry*
C494950:8-aza-5,7-dimethyl-2-trifluoromethylchromone; D000085:Acetates; D001372:Aza Compounds; D002867:Chromones; D005466:Fluorocarbons; D011728:Pyridones; D013438:Sulfhydryl Compounds