Studies On Green Synthetic Technique For Preparing Quinolinone Derivatives

The investigation of 2(1H)-quinolinone derivatives has important meaning on treatment for cardiovascular disease such as myocardial infarct and apoplexy.This paper studied the synthesis of 6-hydroxyl-2(1H)-quinolinone and 4-methyl-6-hydroxyl-2(1H)-quinolinone and their derivatives.The parent bodies of 6-hydroxyl-2(1H)-quinolinone and 4-methyl-6-hydroxyl-2(1H)-quinolinone were synthesized,the reaction methods and green synthetic technology or cleaning technology were discussed,and the technical routes of the parent were explored.The N-vs O-alkylation in 2(1H)-quinolinone derivatives in room temperature ion liquid(RTIL)have been researched,and N-substituted and O-substituted new compounds were synthesized.A novel method was advanced on reducing 6-hydroxyl-2(1H)-quinolinone.With the fast growth of organic chemistry,new organic synthetic techniques come to the fore.Studies related with green chemistry in organic chemistry mainly focus on the following aspects:1)organic synthesis of non-conventional solvent(such as ionic liquid,supercritical fluid);2)Phase Transfer Catalysis;3)solvent free organic synthesis;4)organic synthesis stimulated by microwave;5)Multicomponent Reaction.To be specific,this thesis is a broader study about the feasibility of several kinds of reaction of 2(1H)-quinolinone derivatives with modem green organic synthetic methods.The main work presented in this dissertation is about the investigation on the synthesis of quinolinenones derivatives carried out under green chemical technology or cleaning technology.The contents are listed as the following:1)We have developed an environmentally friendly,economic and efficient synthetic protocol for the preparation of 6-hydroxyl-2(1H)-quinolinone and 4-methyl-6-hydroxyl-2(1H)-quinolinone using solid catalyst under solvent-free conditions at room temperature.2)We developed a very clean,simple and efficient method for the one-pot reactions of preparation of Hydroxyl-3,4-dihydro-2(1H)quinolinone derivatives.The advantages of this method include high yields,short reaction times,and simple work-up.3)We developed a novel approach for preparation of 6-hydroxyl-2(1H)-quinolinone and 4-methyl-6-hydroxyl-2(1H)-quinolinone using ionic liquid which acts as dual solvent-catalyst in promoting the condensation.In addition,at room temperature the ionic liquid 1-butyl-3-methylimidazonium tetrafluoroborate was used as another green recyclable alternatives to volatile organic solvents for the proceses.