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.