Study Of Allylation And Cycloaddition Reactions Based On 2-arylquinazolinones

Quinazolinone is a compound of fuse bicyclic system consisting of benzene ring and pyrimidine ring,which is one of the most important skeletons in heterocyclic ring,which which are widely found in natural products of plant and microbioly with great biological activity,such as: anti-inflammatory,anticonvulsant,antibacterial,antiviral,etc.Main component of many clinical drugs are compose of quinazolinone sketon with various biological properties.Thus,in recent years,the development of anti-cancer drugs has been of interest to a wide range of researchers,and some quinazolinone derivatives have been classified as anti-cancer drugs or alternative drugs due to the relatively outstanding performance of the quinazolinone backbone in the medical field.Therefore,the study of quinazolinone derivatization is of great importance.In addition,transition metal-catalyzed C-H activation is of great interest in organic synthesis,where transition metal-catalyzed C-H activation with2-arylquinazolinones as the directing group has been used to achieve functionalization and conversion to desired compounds.The C-H activation allows regioselective introduction of different groups and highly stereoselective cycloadditions.In this paper,2-arylquinazolinone with 4-vinyl-1,3-dioxolan-2-one and2-(2-azidoethoxy)benzaldehyde were use as raw materials to achieve selective allylation of 2-arylquinazolinone as well as cycloaddition by transition metal-catalyzed.Functional modification of quinazolinone,and ring expansion(six-membered heterocycle and seven-membered heterocycle)of quinazolinone with a series of structurally diverse and potentially biologically active 2-arylquinazolinone derivatives were constructed.The study in this paper has three main parts as follows:(1)2-Arylquinazolinone and 4-Vinyl-1,3-dioxolan-2-one were use as the start materials for the stereoselective synthesis of(E)-allyl alcohol compounds with C-H allylation reaction under transition metal ruthenium catalysis with cesium acetate as base.The reaction was carried out under mild conditions at room temperature with good substrate adaptation and high stereoselectivity.(2)2-Arylquinazolinone and 4-Vinyl-1,3-dioxolan-2-one used as start materials for the C-H/N-H allylation reaction under transition metal cobalt catalyst for the synthesis of alkenyl-substituted cycloaddition products.A range of substrates was well tolerated in the reaction with high yields.(3)A series of benzo-1,4-oxazepine-fused 2-arylquinazolinone compounds were synthesis with C-H amination/cyclization reaction catalyzed by transition metal rhodium using 2-arylquinazolinone and 2-(2-azidoethoxy)benzaldehyde as the start materials.The polycyclic quinazolinone derivatives were synthesis with a one-pot method with good substrate suitability and high yield.