Synthesis Of N,O-Fused Polycyclic Compounds Based On The Cascade Reaction Of 2-Acetyl Benzoic Acid

This paper focuses on the cascade reaction of 2-acetylbenzoic acid.A variety of N,O-fused polycyclic compounds including benzoxazinone,quinazolinone,benzofuranone and benzodiazepine were synthesized,which show broad potential physiological activities.This study provided a simple and efficient synthetic strategy for the construction of heterocyclic rings.The research content of this paper is as follows:Chapter 1:Introduction.N,O-fused polycyclic compounds have become a research hotspot in organic synthesis due to their remarkable physiological and pharmacological activities.This chapter mainly introduces the synthesis and application of benzoxazinone,benzofuranone and benzodiazepines.These related studies have expanded heterocyclic synthesis methods and demonstrated the importance of N,O-fused polycyclic compounds.Chapter 2:Synthesis of isoindole-benzoxazinone/-quinazolinone derivatives.In this chapter,a new one-pot synthetic protocol of benzoxazinone and quinazolinone derivatives without transition metal catalysis is developed.A series of target products with different substituents are synthesized,and the effects of electronic and steric effects of substituents on cyclization are tested.We enriched the methods of the synthesis of benzoxazinone and quinazolinone compounds.Chapter 3:Synthesis of benzofuranone and benzoxazinone derivatives.In this chapter,we develop a novel strategy for the selective synthesis of benzoxazinone or benzofuranone derivatives mediated by different acid/base catalytic systems.This strategy uses cheap and eco-friendly p-TSA or Na₂CO₃ to initiate the cascade reaction between indirubin anhydride and 2-acetyl benzoic acid,and a series of target products can be efficiently obtained.At the same time,the possible reaction mechanism under different catalytic systems was proposed through reasonable design of control experiments.Chapter 4:Synthesis of isoindole-benzo-1,4-diazepines derivatives.In this chapter,a robust method for the synthesis of indole-fused isoindole-benzo-1,4-diazepines is developed.Based on the cascade reaction of 2-acetylbenzoic acid,a series of structural fragments with novel structure and potential physiological activity were obtained under the catalysis of p-TSA through reasonable experimental design.Through the derivatization experiments,it is proved that the compound has strong modifiability and has considerable application prospect.