Synthesis of Hetaryl Substituted Pyrazolo[3,4-b]Quinolinone Systems by Multicomponent Cyclocondensation Reaction

Authors : Mustafa Kemal Gümüş, Şeniz Kaban

Pages : 1204-1216

Doi:10.34248/bsengineering.1545551

View : 74 | Download : 84

Publication Date : 2024-11-15

Article Type : Research Paper

Abstract :In this study, the synthesis of pyrazolo[3,4-b]quinolinone compounds was carried out via one-pot three-component reactions. These reactions proceed as domino processes, making them easier to occur than the conventional multistep organic reactions. By employing this method, new organic molecules can be synthesized in a single step, using minimal time and number of trials. In the first phase of this two-step study, heteroaromatic carbaldehydes (quinoline-8-carboxaldehyde and quinoline-4-carboxaldehyde) were prepared to be used as substrates in subsequent reactions by oxidation of 8-methylquinoline and 4-methylquinoline with selenium dioxide, a mild oxidant. In the second step, heteroaromatic carbaldehyde reacted with aminopyrazole and dimedone in anhydrous ethanol by one-pot multicomponent condensation method to synthesize six compounds with heteryl-substituted pyrazolo[3,4-b]quinolinone ring system. The crude products were obtained in excellent yields and further purified by crystallization. The structures of the compounds, which were found to be completely pure as a result of chromatographic studies, were elucidated by spectroscopic methods and elemental analysis.
Keywords : One Pot reactions, Quinolinone, Selenium dioxide, Methylquinoline, Multicomponent reactions MCRs, Biological activity