Substituted quinolinones. 20. Synthesis of some new 3-heterocyclic quinolinones using 2i-3-(3-(dimethylamino)-acryloyl)-1-ethyi-4- hydroxyquinolin-2(1H)-one

摘要

Treatment of E-3-(3-(dimethylamino)acryloyl)-1-ethyl-4-hydroxyquinolin-2(1H)-one with glacial acetic acid and/or thionyl chloride afforded pyrano[3,2-c]quinoline-4,5-diones while its a-electrophilic substitution reactions with allyl isothiocyanate and p-nitrobenezenediazonium chloride furnished the N-allylthioamide and arylazo-enol derivatives. The latter arylazo-enol derivative was subjected to heterocyclization some active methylene esters affording new pyrazole and pyridazine derivatives. The reaction of the titled enaminone with some 1,2-, 1,3-, and 1,4-binucleophilic reagents led to formation of novel quinolinones bearing various five-, six, and seven-membered heterocyclic substituents at position-3.