Substituted quinolinones. Part 13 a convenient route to heterocyclization reactions with 3-substituted 4-hydroxyquinolin-2(1H)-one

Abstract

(Chemical Equation Presented) The reactivity of 3-[(dimethylamino)prop-2- enoyl]-4-hydroxyl-1-methylquinolin-2(1H)-one (2) towards different nucleophilic and electrophilic reagents was investigated. The convenient synthesis of several 3-heterocyclyl-quinolinones such as 3-pyridazinyl- 10, 11, 3-pyranyl 19a,b and 3-pyrazolylquinolinones 20a,b, 22, 26a,b, 27a,b, 31 and 33 has been described starting from the 3-acetylquinolinone 1 and enaminone 2. In addition, certain heterocyclo[c]quinolinones such as pyrimido- 12, 14 pyrano- 3, 17a,b and pyrazolopyranoquinolinone 29 were obtained in good yields.