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香豆素并[4,3-b]喹啉-6-酮类化合物的合成与表征 被引量：2

Synthesis and Characterization of Chromeno [4,3-b] Quinolin-6-ones
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摘要 以浓硫酸为催化剂,在绿色环保的水作溶剂的条件下,以6-取代-4-氯-3-醛基香豆素和取代苯胺为原料,通过亲核取代、环缩合"一锅"反应合成得到目标化合物,产率中等至较优,最高可达91%。此法合成试剂来源方便,操作简单,同时避免了有毒有害溶剂的使用。 One-pot reaction of substituted 4-chloro-3-formylcoumarins and different substituted anilines was studied. A seires of chromeno[4,3-b]quinolin-6-ones were synthesized conviently and in 66% - 91% yield with a few drops of concentrated sulfuric acid as catalyst and H2 O as solvent at 60 - 70 ℃. The structures were confirmed by melting point,IR,NMR spectroscopy. Obviously the protocol offers the advantages of cheap reagents,straightforward procedures and avoids the requirement of poisonous and harmful solvents.
作者 曾竟 喻雅婷 郭秀秀 申凰林
机构地区 新疆师范大学化学化工学院
出处 《化学试剂》 CAS 北大核心 2015年第9期854-856,864,共4页 Chemical Reagents
基金 新疆维吾尔自治区高校科研计划青年项目(XJEDU2014S038)
关键词 香豆素并[4 3-b]喹啉-6-酮 浓硫酸 水 chromeno[4 3-b]quinolin-6-ones concentrated sulfuric acid H2O
分类号 O626 [理学—有机化学]
  • 相关文献

参考文献12

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  • 4HEBER D. Reactions on heterocycles containing 2-aeyl-2- propenone structure. VI. novel preparation of 6-oxo-6H- [ 1 ] benzopyrano [ 4,3-b ] quinoline derivatives [ J ]. Arch. Pharm. , 1987,320(7 ) :595-599.
  • 5TABAKOVIC K, TABAKOVIC I, AJDIAI N, et al. A no- vel transformation of 4-(arylamino) coumarins to 6H-1- benzopyrano [ 4, 3-b I quinolin-6-ones under Vilsmeier- Haaek conditions [ J ]. Synthesis, 1987, ( 3 ) : 308-310.
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  • 10HAMDI N,FISCHMEISTER C,PUERTA M C,et al. A rapid access to new coumarinyl chalcone and substituted chromeno [ 4,3-c ] pyrazol-4 ( 1H ) -ones and their anti-bacterial and DPPH radical scavenging activities [ J ]. Med. Chem. Res. , 2011 , 20 ( 4 ) : 522-530.

二级参考文献5

同被引文献18

  • 1陈治宇,刘丽艳,王宏伟.异喹啉生物碱类化合物的合成及其血管紧张素Ⅱ受体拮抗活性[J].化学试剂,2005,27(7):422-424. 被引量：1
  • 2Barot K P,Jain S V,Kremer L,et al. Recent advances and therapeutic journey of coumarins : current status and per- spectives [ J ]. Med Chem Res,2015,24 ( 7 ) :2 771-2 798.
  • 3Emami S, Dadashpour S. Current developments of couma- rin-based anti-cancer agents in medicinal chemistry [ J ]. Eur J Med Chem,2015,102:611-630.
  • 4Grover J,Jachak S M. Coumarins as privileged scaffold for anti-inflammatory drug development [ J ]. RSC Adv,2015,5 (49) :38892-38905.
  • 5Mulakayala N, Rambabu D, Raja M R, et al. Ultrasound mediated catalyst free synthesis of 6H-1 -benzopyrano [ 4,3- b] quinolin-6-ones leading to novel quinoline derivatives: their evaluation as potential anti-cancer agents [ J ]. Bioorg Med Chem,2012,20( 2 ) :759-768.
  • 6Heber D, Reactions on heterocycles containing 2-acyl-2- propenone structure. VI. novel preparation of 6-oxo-6H- [ 1 ] benzopyrano [ 4,3-b ] quinoline derivatives [ J ]. Arch Pharm ( Weinheim, Ger. ), 1987,320 ( 7 ) : 595-599.
  • 7Tabakovic K, Tabakovic I, Ajdini N, et al. A novel trans- formation of 4-(arylamino) coumarins to 6H-I-Benzopyra- no[4,3-b] quinolin-6-ones under Vilsmeier-Haack condi- tions[ J]. Synthesis, 1987, (3) :308-310.
  • 8Mohammadian R, Sanderos R, Nazifi A, et al. New cata- lyzed way to prepare chromeno [ 4,3-b ] quinolin-6-ones [J]. Inorg Chem Indian J,2015,10(1) :27-30.
  • 9Prasad J V, Reddy J S, Kumar N R, et al. An efficient ul- trasound promoted catalyst-free protocol for the synthesis of chromeno [ 4, 3-b ] quinolin-6-ones [ J ]. J Chem Sci ( Bangalore, India ), 2011,123 ( 5 ) : 673 -679.
  • 10Wu J, Wang X, Facile synthesis of chromeno [ 4,3-b ] quin- olin-6-ones from unexpected reactions of aryl isocyanides with 4-chloro-2-oxo-2H-chromene-3-carbaldehyde [ J ]. Org Biomol Chem,2006,4(7) :1 348-1 351.

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化学试剂
2015年 第9期

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