Synthesis of new hydroquinolinone compounds

Heterocyclics and their derivatives are very important compounds due to their biological effects. Therefore, very extensive studies for the synthesizing of that kind of compounds have been done in recent years. Thus, the heterocyclic compounds containing atoms such as nitrogen, sulfur and oxygen as ring member are widely used both in various fields of industry and medicine. As a result of the data obtained from the literature and patent investigations, it has been discovered that hydroquinolinone compounds show biological activity such as anti-bacterial, anti-hypertensive, anti-psychotic and neuroleptic. Besides, these compounds are important precursors in the synthesis of natural products such as alkaloids, azastereoids and toxins. Therefore, this research has been planned by the purpose of the synthesis of some new hetaryl-substituted hydroquinolinone derivatives that they may be useful in the biochemical and pharmaceutical areas. In the first step of the study which has been made as three stages, three hetarylideneisopropylidenemalonate compounds, one of these is original, have been synthesized via Knoevenagel reaction using various hetarylaldehydes and Meldrum?s acid. As for the second step, five enaminone compounds, which three ones of these are new compounds, have been synthesized by the reaction of various aromatic amines with dimedone. Both Knoevenagel products and enaminone compounds have been obtained in rather good yields (82-94%). In the last step which is the most important stage of the study, seven new 1-aryl-7,7-dimethyl- 4-hetaryl-1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione compounds have been synthesized, by using the materials produced in the first and the second steps, in the yields of 40-50% as a result of Michael addition reaction and then elimination reaction which are taken place in the media of acetic acid. Addition to these products, biochemically important five new hydroacridinone derivatives have also been obtained as by-products. Optimum circumstances have been established using various reaction conditions and catalyzers throughout the research. The structures of all synthesized compounds have been clarified by ultraviolet, infrared, nuclear magnetic resonance and mass spectral methods. Keywords: Hetarylaldehyde, Knoevenagel reaction, Meldrum?s acid, dimedone, enamine, Michael addition, hydroquinolinone, hydroacridinone.