3-氨基-7,8-二甲氧基-2(1H)-喹诺酮的合成
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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); 药用资源化学与药物分子工程教育部重点实验室资助课题(CMEMR2015-B03)


The Synthesis of the 3-amino-7,8-dimethyl-2(H)-quinolone
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    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(IV)计可达70%以上。

    Abstract:

    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 as the reduced system 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.

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宋健,陈明杰.3-氨基-7,8-二甲氧基-2(1H)-喹诺酮的合成[J].精细化工,2016,33(3):

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  • 收稿日期:2015-12-07
  • 最后修改日期:2016-01-26
  • 录用日期:2016-02-02
  • 在线发布日期: 2016-03-03
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