Rhodium-Catalyzed Ortho C-H Functionalization Of 2-Aryl Quinazoline Derivatives

Quinazoline derivatives are important heterocycles bearing good biological and pharmacological activity. Most of drug molecules and natural products containing a quinazoline skeleton exhibit unique properties in diuresis, anti-inflammatory and anticonvulsants.In the past decades, functionalization realized by transition-metal-mediated C-H activation has recently attracted considerable attention from synthetic chemists,because it offers a direct, rapid, simple and selective route to a series of useful compounds. Recently, our group found quinazoline skeleton has multiple reactive sites which can selectively realize functionalization under the effect of transition metals. Therefore, we proposed to realize ortho C-H bond functionalization of 2-aryl quinazoline derivatives catalyzed by Rhodium.This thesis is divided into three parts.The first chapter mainly elaborated the development of the synthetic reaction of quinazoline derivatives under the condition of transition metal palladium, copper and metal free in recent years. The second chapter mainly depicted the implementation of quinazolinone compounds C-H functionalization to get a series of quinazoline ketone derivatives through Rhodium catalysis and Aza-Michale addition. This method has emerged as an atom economical and high efficiency. And the formation of C-C bonds and C-N bond rapidly through tandem reaction is of importance guiding significance to the derivatization of quinazolinone. The third chapter mainly stated the reaction of quinazoline derivatives with diazo that implements the double C-H functionalization of 2,4-diaryl quinazoline derivatives under rhodium catalysis, the reaction can go ahead only need tiny amounts of transition metal.