A convenient one-pot synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one

被引:116
|
作者
Jung, JC [1 ]
Jung, YJ [1 ]
Park, OS [1 ]
机构
[1] Chungbuk Natl Univ, Coll Nat Sci, Dept Chem, Cheongju 361763, Chungbuk, South Korea
关键词
D O I
10.1081/SCC-100104003
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An improved one-pot synthesis of 4-hydroxycoumarin. 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one from 2-hydroxyacetophenone, 2-mercaptoacetophenone, and 2-aminoacetophenone, respectively, is described. The synthetic strategies involve the acylation and internal ring cyclization. This method is readily amenable to large-scale synthesis of 4-hydroxycoumarin, 4-hydroxythiocoumarin, and 4-hydroxyquinolin-2(1H)-one derivatives in high yields.
引用
收藏
页码:1195 / 1200
页数:6
相关论文
共 50 条
  • [1] CLEAN AND CONVENIENT ONE-POT SYNTHESIS OF 4-HYDROXYCOUMARIN AND 4-HYDROXY-2-QUINOLINONE DERIVATIVES
    Gao, Wen-Tao
    Hou, Wen-Duan
    Zheng, Mei-Ru
    Tang, Li-Jun
    SYNTHETIC COMMUNICATIONS, 2010, 40 (05) : 732 - 738
  • [2] Three-component reaction between triphenylphosphine, acetylenic esters and 4-hydroxycoumarin, 4-(phenylamino)coumarin, 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-1-methylquinolin-2(1H)-one
    Anary-Abbasinejad, Mohammad
    Anaraki-Ardakani, Hossein
    Ezadi, Ali
    Hassanabadi, Alireza
    JOURNAL OF CHEMICAL RESEARCH, 2007, (10) : 605 - 608
  • [3] Synthesis of 4-hydroxyquinolin-2(1H)-one analogues and 2-substituted quinolone derivatives
    Jung, JC
    Jung, YJ
    Park, OS
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (01) : 61 - 67
  • [4] Reactions of 4-Hydroxyquinolin-2(1H)-ones with Acenaphthoquinone: Synthesis of New 1,2-Dihydroacenaphthylene-spiro-tetrakis(4-hydroxyquinolin-2(1H)-ones)
    Aly, Ashraf A.
    Ramadan, Mohamed
    El-Reedy, Ahmed A. M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2019, 56 (02) : 642 - 645
  • [5] Water mediated efficient one-pot synthesis of bis-(4-hydroxycoumarin)methanes
    Sangshetti, Jaiprakash N.
    Kokare, Nagnnath D.
    Shinde, Devanand B.
    GREEN CHEMISTRY LETTERS AND REVIEWS, 2009, 2 (04) : 233 - 235
  • [6] 4-hydroxyquinolin-2(1H)-one isolated in cryogenic argon and xenon matrices: Tautomers and photochemistry
    Secrieru, A.
    Lopes, S.
    Nikitin, T.
    Cristiano, Maria L. S.
    Fausto, R.
    JOURNAL OF MOLECULAR STRUCTURE, 2024, 1312
  • [7] Design, synthesis and antitubercular potency of 4-hydroxyquinolin-2(1H)-ones
    de Macedo, Maira Bidart
    Kimmel, Roman
    Urankar, Damijana
    Gazvoda, Martin
    Peixoto, Antonio
    Cools, Freya
    Torfs, Eveline
    Verschaeve, Luc
    Lima, Emerson Silva
    Lycka, Antonin
    Milicevic, David
    Klasek, Antonin
    Cos, Paul
    Kafka, Stanislav
    Kosmrlj, Janez
    Cappoen, Davie
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 138 : 491 - 500
  • [8] A facile and convenient approach for the one-pot synthesis of 2,4(1H,3H)-quinazolinediones
    Sharafi-Kolkeshvandi, Mahnaz
    Nikpour, Farzad
    CHINESE CHEMICAL LETTERS, 2012, 23 (04) : 431 - 433
  • [9] A facile and convenient approach for the one-pot synthesis of 2,4(1H,3H)-quinazolinediones
    Mahnaz Sharafi-Kolkeshvandi
    Farzad Nikpour
    Chinese Chemical Letters, 2012, 23 (04) : 431 - 433
  • [10] One-pot and chemoselective synthesis of bis(4-hydroxycoumarin) derivatives catalyzed by nano silica chloride
    Karimian R.
    Piri F.
    Safari A.A.
    Davarpanah S.J.
    Journal of Nanostructure in Chemistry, 2013, 3 (1)