A mild and efficient method for large scale synthesis of 3-aminocoumarins and its further application for the preparation of 4-bromo-3-aminocoumarins

被引:16
作者
Das, Deb K. [1 ]
Sarkar, Satavisha [1 ]
Khan, Musawwer [3 ]
Belal, Md. [1 ]
Khan, Abu T. [1 ,2 ]
机构
[1] Indian Inst Technol Guwahati, Dept Chem, Gauhati 781039, India
[2] Aliah Univ, Kolkata 700091, W Bengal, India
[3] Aligarh Muslim Univ, Dept Chem, Aligarh 202002, Uttar Pradesh, India
关键词
3-Acetamidocoumarins; 3-Aminocoumarins; Salicylaldehydes; N-Acetylglycine; Sulfuric acid; BIOLOGICAL EVALUATION; BROMODIMETHYLSULFONIUM BROMIDE; DERIVATIVES; NOVOBIOCIN; INHIBITORS; COUMARINS; TRANSFORMATIONS; BROMINATION; PREVENTION; PYRROLES;
D O I
10.1016/j.tetlet.2014.07.035
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A wide variety of 3-aminocoumarins have been synthesized in large scale from the corresponding 3-acetamidocoumarins by regioselective cleavage of carbon-nitrogen bond using 70% sulfuric acid under reflux conditions. The synthesized 3-aminocoumarins were further brominated regioselectively at the 4-position of 3-aminocoumarin using BDMS as brominating agent. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4869 / 4874
页数:6
相关论文
共 63 条
  • [1] [Anonymous], 1982, NATURAL COUMARINS OC, DOI DOI 10.1016/0160-9327(83)90060-1
  • [2] A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction
    Audisio, Davide
    Messaoudi, Samir
    Peyrat, Jean-Francois
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. TETRAHEDRON LETTERS, 2007, 48 (39) : 6928 - 6932
  • [3] A Simple Synthesis of Functionalized 3-Bromocoumarins by a One-Pot Three-Component Reaction
    Audisio, Davide
    Messaoudi, Samir
    Brion, Jean-Daniel
    Alami, Mouad
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (06) : 1046 - 1051
  • [4] COUMESTROL, A NEW ESTROGEN ISOLATED FROM FORAGE CROPS
    BICKOFF, EM
    BOOTH, AN
    LYMAN, RL
    LIVINGSTON, AL
    THOMPSON, CR
    DEEDS, F
    [J]. SCIENCE, 1957, 126 (3280) : 969 - 970
  • [5] Synthesis of new 2H,4H-benzopyrano[3,4-b]pyridine-1,3,5-trione derivatives via carbon suboxide
    Bonsignore, L
    Loy, G
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, 35 (01) : 117 - 119
  • [6] Chakravarti D., 1965, CURR SCI INDIA, P177
  • [7] Dioxane dibromide mediated bromination of substituted coumarins under solvent-free conditions
    Chaudhuri, Subrata Kumar
    Roy, Sanchita
    Bhar, Sanjay
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2012, 8 : 323 - 329
  • [8] Recent advances in the application of bromodimethylsulfonium bromide (BDMS) in organic synthesis
    Choudhury, Lokman H.
    Parvin, Tasneem
    Khan, Abu T.
    [J]. TETRAHEDRON, 2009, 65 (46) : 9513 - 9526
  • [9] Dakin HD, 1929, J BIOL CHEM, V82, P439
  • [10] Synthesis of fused tetrahydropyrido[2,3-c]-coumarin derivatives as potential inhibitors for dopamine d3 receptors, catalyzed by hydrated ferric sulfate
    Das, Deb K.
    Sarkar, Satavisha
    Khan, Abu T.
    Saravanan, Parameswaran
    Patra, Sanjukta
    [J]. RSC ADVANCES, 2014, 4 (07): : 3581 - 3590