摘要
为了改进和优化3-氨基-2(1H)-喹诺酮环的合成工艺,从芳草醛出发,依次经过乙酰化、硝化、甲基化、还原,制备出2-氨基-3,4-二甲氧基苯甲醛(Ⅴ),Ⅴ与硝基乙酸甲酯环合得3-硝基-7,8-二甲氧基-2(1H)喹诺酮(Ⅵ),还原Ⅵ,得到3-氨基-7,8-二甲氧基-2(1H)-喹诺酮。优化后的环合条件为:以体积比7∶3的甲苯和环己烷为混合溶剂,哌啶为催化剂;Ⅵ最佳还原条件为:乙醇为溶剂,5%钯碳和甲酸铵为还原剂。在该条件下,3-氨基-7,8-二甲氧基-2(1H)-喹诺酮合成总收率从邻氨基苯甲醛(Ⅴ)计可达70%以上。
To improve and optimize the synthetic process of 3-amino-2（ 1H）-quinolone ring,3-amino-7,8-dimethoxyl-2（ 1H）-quinolone（ Ⅶ） was synthesized by the reduction of 3-nitro-7,8-dimethoxyl-2（ 1H）-quinolone（ Ⅳ）,which was prepared by the cyclization of 2-amino-3,4-dimethoxylbenzaldehyde（ Ⅴ） with methyl nitroacetate. The compound Ⅴ was successively prepared from vanillin via actylation,nitrolation,methylation and reduction. The results showed that preferred synthetic conditions were as following： the piperidine catalyzed the cyclization reaction in the mixed solvent of toluene and cyclohexane in volume ratio 7 ∶ 3,the 5% Pd / C and ammonium formate were used to reduce the compound Ⅵ. The synthetic yield of the 3-amino-7,8-dimethoxyl-2（ 1H）-quinolone could reach higher than 70%,calculated from the O-aminobenzaldehyde Ⅴ.
出处
《精细化工》
EI
CAS
CSCD
北大核心
2016年第3期357-360,共4页
Fine Chemicals
基金
广东省科技计划资助项目(2010B060900084)
中国博士后基金资助项目([2010]07)
省部共建药用资源化学与药物分子工程国家重点实验室资助课题(CMEMR2015-B03)~~
