Bicyclic Pyrrole And The Bicyclic Pyridone Heterocyclic Compounds Synthesized Research

N-heterocycles are the important compounds with good biological activities and extensive properties causing attention of chemists. In recent few years, there are many N-containing heterocycles were developed into medicines and pesticides. Most N-heterocyclic pesticides have low toxicity to mammals, birds and fish, and with high selectivity to insects and bacteria.Bicyclic pyrroles have excellent biological activities such as anticancer, antibacterial, analgesic, anti-inflammatory, and so on. For instance, bicyclic pyrroles used as protein kinase CK2inhibitors and5HT4-receptor antagonists. Bicyclic pyridones have excellent biological activities including anticancer, analgestic, antiphlogistic activities. They were frequently found in pharmacophores like camptothecin and huperzine. The main research contents and results as follows:1. The benzoyl substituted mercaptals2were synthesized by acetophenone derivatives1. Compound2reacted with ethane-1,2-diamine, propane-1,3-diamine or butane-1,4-diamine to obtain the heterocyclic ketene aminals3.2. In this thesis, cheap and.easily attained diethyl but-2-ynedioate or ethyl propiolate S and iodine were used as raw materials. Ethyl2,3-diiodoacrylate or diethyl2,3-diiodofumarate6were synthesized with good yields in CHCl3and under reflux conditions. The synthetic method has the advantages of very simple and efficient.3. A method of synthesis novel bicyclic pyrroles/pyridones have been constructed by cyclic condensation of heterocyclic ketene aminals (HKAs)3with Ethyl2,3-diiodoacrylate or diethyl2,3-diiodofumarate6in the presence of PdCl2/CszCO3as catalyst. The method has the advantages of very simple and efficient. Twenty novel bicyclic pyrroles7a-7t were synthesized with71-93%, seven novel bicyclic pyridones8a-8b and9a-9e were synthesized with43-62%.4. All the structures of the target compounds were characterized by IR,1H NMR,13C NMR and HRMS, The structure of7g was characterized by X-ray. The target compounds had not been reported in literatures.5. The synthesis and applications of bicyclic pyrrole/pyridones were also reviewed in this thesis.