Synthesis And Characteirzation Of Novel Heterocycles Containing Quinolines Skeleton

Quinoline ring is a back-bone of many natural products and pharmacologically significantcompounds displaying a broad range of biological activity. Especially, heterocyclic compoundsfused to a quinoline ring are found in many natural products as well as in synthetic compounds.In this thesis, we selected ethyl2-（chloromethyl）)quinoline-3-carboxylate as starting compoundto synthesize a variety of heterocyclic compounds. The thesis was mainly consisted of five parts.In the first part, the property, synthesis and application of quinoline and its derivatives aswell as the application of oximes are reviewed.In the second part, improved synthesis of ethyl2-（chloromethyl）quinoline-3-carboxylate （1）was described using ZnCl₂and SnCl₂as catalyst in the presence of ethanol as solvent. The yieldof compound1was in82.3%yield and its structure confirmed by IR, MS, and NMR.In the third part, ethyl2-（chloromethyl）quinoline-3-carboxylate （1） reacted with2-hydroxy-phenylethanone derivates （2a-g） under Williamson reaction conditions to give2-（3-methyl-benzofuran-2-yl）quinoline-3-carboxylic acid derivates （3a-g） in62.7-80.2%yields. Thestructures of （3a-g） were confirmed by spectral data.In the fourth part, ethyl2-（chloromethyl）quinoline-3-carboxylate （1） reacted with anilinederivatives （5a-g） under Williamson reaction conditions to giving the corresponding2-phenyl-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-one derivates （6a-e） and ethyl2-（（phenylamino）methyl）quinoline-3-carboxylate derivates （6f-g） in73.6-84.4%yields. The structures of （6a-g）were confirmed by spectral data.In the fifth part,3-oxa-acridone was first synthesized from ethyl2-（chloromethyl）quinoline-3-carboxylate （1） as the starting material according to previous literature. Then theresulting3-oxa-acridone was used as a key substrate to react with formylferrocene through fourdifferent methods to give the corresponding3-ethylidene ferrocenyl-1H–pyrano[3,4-b]quinolin-4（3H）-one（7）. Besides,3-oxa-acridone was reacted with hydroxylamine hydrochloridein the presence of ethanol as solvent to give3-oxa-acridone oxime （8） in83.3%yield, which wasunderwent acylation reaction with benzoyl chloride and benzenesulfonyl chloride in an alkalinecondition to yield the compounds （9a-b）. The structures of （7-9） were confirmed by IR, NMR,and MS.