Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines

被引:18
作者
Deshmukh, Amarsinh [1 ]
Gore, Babasaheb [1 ]
Thulasiram, Hirekodathakallu V. [2 ]
Swamy, Vincent P. [1 ]
机构
[1] CSIR Natl Chem Lab, Organ Chem Div, Pune 411008, Maharashtra, India
[2] CSIR Natl Chem Lab, Chem Biol Unit, Pune 411008, Maharashtra, India
关键词
QUATERNARY AMMONIUM POLYHALIDES; BENZYLTRIMETHYLAMMONIUM DICHLOROIODATE; N-IODOSUCCINIMIDE; EFFICIENT METHOD; GREEN SOLVENTS; HALOGENATION; ARENES; MILD; PHENOLS; ACID;
D O I
10.1039/c5ra14702f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.
引用
收藏
页码:88311 / 88315
页数:5
相关论文
共 54 条
  • [1] A new, environment friendly protocol for iodination of electron-rich aromatic compounds
    Adimurthy, S
    Ramachandraiah, G
    Ghosh, PK
    Bedekar, AV
    [J]. TETRAHEDRON LETTERS, 2003, 44 (27) : 5099 - 5101
  • [2] Alexander VM, 2003, SYNLETT, P1895
  • [3] REGIOSELECTIVE IODINATION OF ARYL AMINES USING 1,4-DIBENZYL-1,4-DIAZONIABICYCLO [2.2.2] OCTANE DICHLOROIODATE IN SOLUTION AND UNDER SOLVENT-FREE CONDITIONS
    Alikarami, Mohammad
    Nazarzadeh, Somayeh
    Soleiman-Beigi, Mohammad
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2015, 29 (01) : 157 - 162
  • [4] A mild, efficient and selective iodination of aromatic compounds using iodine and 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate
    Badri, Rashid
    Gorjizadeh, Maryam
    [J]. CHINESE CHEMICAL LETTERS, 2009, 20 (12) : 1439 - 1443
  • [5] Regioselective iodination of arenes using iodine/NaBO3 • 4H2O system in ionic liquid
    Bhilare, Sachin V.
    Deorukhkar, Amol R.
    Darvatkar, Nitin B.
    Salunkhe, Manikrao M.
    [J]. SYNTHETIC COMMUNICATIONS, 2008, 38 (17) : 2881 - 2888
  • [6] THE IODINATION OF AROMATIC SUBSTRATES ON ALUMINA
    BOOTHE, R
    DIAL, C
    CONAWAY, R
    PAGNI, RM
    KABALKA, GW
    [J]. TETRAHEDRON LETTERS, 1986, 27 (20) : 2207 - 2210
  • [7] MILD, EFFICIENT, AND REGIOSELECTIVE MONOBROMINATION OF ARYLAMINES AND PHENOLS USING [BBIm]Br3 AS A NEW REAGENT
    Borikar, Sanjay P.
    Daniel, Thomas
    Paul, Vincent
    [J]. SYNTHETIC COMMUNICATIONS, 2010, 40 (05) : 647 - 653
  • [8] Trihalide-based ionic liquids. Reagent-solvents for stereoselective iodination of alkenes and alkynes
    Bortolini, O
    Bottai, M
    Chiappe, C
    Conte, V
    Pieraccini, D
    [J]. GREEN CHEMISTRY, 2002, 4 (06) : 621 - 627
  • [9] Mild and regioselective iodination of electron-rich aromatics with N-iodosuccinimide and catalytic trifluoroacetic acid
    Castanet, AS
    Colobert, F
    Broutin, PE
    [J]. TETRAHEDRON LETTERS, 2002, 43 (29) : 5047 - 5048
  • [10] Cooper G. K., 1984, US Pat., Patent No. [US4465864, 4465864]