Design,Synthesis And Characterization Of Condensed Heterocyclic Compound Containing Iodo Substituent Quinoline Skeleton

Quinoline and its derivatives are typical kind of nitrogen heterocyclic compounds,they occupy a very important position in biological and pharmacological activity.So 6-Iodoquinolines are also widely applied in the fields of organic ligand and medical field.In this thesis,Iodo substituent quinion skeleton compounds were selected as the substrate to conduct the reaction with a series of compounds（such as amines,phenols etc.）and a veriety of 6-iodoquinoline-based compounds were synthesized successfully.The thesis is mainly consisted of six parts as follows:In the first part,The biological and pharmaceutical activities of quinoline skeleton compounds were reviewed.The second part,Acetaminophenone and 2-Aminobenzophenone is used as the starting compound,the synthetic route of iode substituent quinolone carboxylate been designed.first,the iode substituent reaction is studied,obtained the 3-iode substituent and 3,5-2-iode substituent compound（1a-1d）.Then continue the react with 3-iode substituent（1a,1b）,obtained the ethyl 2,4-bis（chloromethyl）-6-iodoquinoline-3-carboxylate（1e）and 2-（chloromethyl）-6-iodo-4-phenylquinoline-3-carboxylate（1f）,and use it as the starting compound to expand the next research.The thired part,compound 1e is used as the starting compound,reacted with phenol or substituted phenols in one-pot procedure with presence of potassium carbonate as the base and acetonitrile as solvent to give corresponding 6-iode-2,4-（phenoxymethyl）quinoline-3-carboxylic acids derivatives（2a-2n）.In the fourth part,compound 1e is used as the starting compound,reaction in the presence of K₂CO₃ as acid-binding agent,MeCN as solvent and PEG-400 as phase transfer catalyst with corresponding salicylaldehydes,involving three-step one-pot reaction,a facile synthesis of 2,4-2-（benzofuran-2-yl）-6-iode-3-carboxylic acid derivatives has been described.In the fifth part,the synthesis of a series of novel（E）-6-iode-2,4-2-arylvinylquinoline-3-carboxylic acid derivatives（4a-4q）had been achieved through a simple and efficient one-pot reaction of 1e with various aromatic aldehydes,involving the reaction of 1e with triethyl phosphate followed by the Wittig-Horner reaction with various aromatic aldehydes using NaH/DMF system and subsequent basic hydrolysis.In the last part,1f as the starting compound was subjected to the reaction with various amines reaction in anhydrous ethanol,obtained the7-iode-9-phenyl-[3,4-b]quinolin-1-one derivatives（5a-5h）.Structure of synthesized compounds 1a-1f,2a-2n,3a-3i,4a-4q and5a-5h characterized by IR,¹H NMR,¹³C NMR and HRMS spectra.