GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions

被引:69
作者
Wang, Huiyan [1 ,2 ]
Liu, Xuecheng [1 ]
Feng, Xian [1 ]
Huang, Zhibin [1 ]
Shi, Daqing [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
[2] Huaihai Inst Technol, Dept Chem Engn, Lianyungang 222005, Peoples R China
关键词
FORMAL TOTAL-SYNTHESIS; SPIROOXINDOLE DERIVATIVES; POLYSUBSTITUTED PYRROLES; REGIOSELECTIVE SYNTHESIS; 3-COMPONENT REACTION; N; S-KETENE ACETAL; DOMINO REACTION; ACCESS; COPPER; KNORR;
D O I
10.1039/c3gc41799a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A concise and efficient one-pot synthesis of pyrrolyl coumarin derivatives via a four-component reaction of 4-hydroxycoumarin, arylglyoxal monohydrate, dialkyl but-2-ynedioate and amines under catalyst-free conditions in an environmentally friendly medium (ethanol) is described. This synthesis was confirmed to follow the group-assisted-purification (GAP) chemistry process, which can avoid traditional chromatography and recrystallization purification methods.
引用
收藏
页码:3307 / 3311
页数:5
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共 71 条
  • [1] Silica-supported bismuth(III) chloride as a new recyclable heterogeneous catalyst for the Paal-Knorr pyrrole synthesis
    Aghapoor, Kioumars
    Ebadi-Nia, Leila
    Mohsenzadeh, Farshid
    Morad, Mina Mohebi
    Balavar, Yadollah
    Darabi, Hossein Reza
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2012, 708 : 25 - 30
  • [2] Total syntheses of ningalin A, lamellarin O, lukianol A, and permethyl storniamide A utilizing heterocyclic azadiene Diels-Alder reactions
    Boger, DL
    Boyce, CW
    Labroli, MA
    Sehon, CA
    Jin, Q
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (01) : 54 - 62
  • [3] A novel microwave-mediated one-pot synthesis of indolizines via a three-component reaction
    Bora, U
    Saikia, A
    Boruah, RC
    [J]. ORGANIC LETTERS, 2003, 5 (04) : 435 - 438
  • [4] Highly efficient construction of pentacyclic benzo[b]indeno-[1,2,3-de][1,8]naphthyridine derivatives via four-component domino reaction
    Cao, Cheng-Pao
    Lin, Wei
    Hu, Ming-Hua
    Huang, Zhi-Bin
    Shi, Da-Qing
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (62) : 6983 - 6985
  • [5] Competing Knorr and Fischer-Fink pathways to pyrroles in neutral aqueous solution
    Chandrashaker, Vanampally
    Taniguchi, Masahiko
    Ptaszek, Marcin
    Lindsey, Jonathan S.
    [J]. TETRAHEDRON, 2012, 68 (34) : 6957 - 6967
  • [6] Efficient one-pot synthesis of spiro[indoline-3,4′-pyrazolo[3,4-e][1,4]thiazepine]dione via three-component reaction
    Chen, Hui
    Shi, Daqing
    [J]. TETRAHEDRON, 2011, 67 (31) : 5686 - 5692
  • [7] Efficient One-Pot Synthesis of Novell Spirooxindole Derivatives via Three-Component Reaction in Aqueous Medium
    Chen, Hui
    Shi, Daqing
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2010, 12 (04): : 571 - 576
  • [8] Synthesis of polysubstituted N-H pyrroles from vinyl azides and 1,3-dicarbonyl compounds
    Chiba, Shunsuke
    Wang, Yi-Feng
    Lapointe, Guillaume
    Narasaka, Koichi
    [J]. ORGANIC LETTERS, 2008, 10 (02) : 313 - 316
  • [9] Polyenylpyrroles and polyenylfurans from an Australian isolate of the soil ascomycete Gymnoascus reessii
    Clark, BR
    Capon, RJ
    Lacey, E
    Tennant, S
    Gill, JH
    [J]. ORGANIC LETTERS, 2006, 8 (04) : 701 - 704
  • [10] Diradical dications of m- and p-phenylenebis[2,5-di(2-thienyl)-1-pyrrole]:: Weakly coupled diradicals
    Domingo, VM
    Alemán, C
    Brillas, E
    Juliá, L
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (11) : 4058 - 4061