Study On The Metal-Free Oxidative Formylation Of Quinazolinones Using Benzyne

Formamide compounds are widely used in organic synthesis and medicinal chemistry.The most basic formamide（CH₃NO）is an important raw material for synthetic medicine and industrial dyes.It can also be used as a solvent for spinning synthetic fibers,plastic processing,and wood casein.Ink production,etc.Formamide is also considered to be an important basic structural unit in compounds.Because it often appears in the structural framework of many natural products and biologically active molecules,it exhibits diverse biological characteristics and has attracted the interest of many medicinal chemists.Under normal circumstances,the preparation of formamide is achieved by using formylation reagents,and the method of preparing formamide compounds by oxidative formylation without metal participation is rarely reported.Therefore,it is of great significance to develop an effective oxidative formylation reaction strategy without metal participation to synthesize formamide compounds.In this paper,a series of carboxamide compounds are prepared by using benzyne as a highly reactive intermediate to initiate the ring opening of quinazolinones,without metal catalysis and achieving oxidative formylation under mild reaction conditions.In the first chapter of this thesis,a series of medicinal applications and synthesis methods of a series of formamide compounds are described.In the second chapter,using different quinazolinone and benzyne precursors as raw materials,under simple conditions,a series of carboxamide compounds were obtained with a yield of50-90%.After that,the mechanism of the reaction was explored,and the course of the reaction was inferred and corroborated.Based on the mechanism,the reaction was further expanded and studied.All compounds were characterized by nuclear magnetic resonance and mass spectrometry.Among them,single crystal culture and X-Ray characterization of 4e were carried out.