Facile synthesis of azaarene-2-substituted chromanone derivatives via tandem sp3 C-H functionalization/decarboxylation of azaarenes with 4-oxo-4H-chromene-3-carboxylic acid

被引：29
作者：
Shao, Zhuzhou [1 ]
Wang, Liang [1 ]
Xu, Lubin [1 ]
Zhao, Huaili [1 ]
Xiao, Jian [1 ]
机构：
[1] Qingdao Agr Univ, Coll Chem & Pharmaceut Sci, Qingdao 266109, Peoples R China
来源：
RSC ADVANCES | 2014年 / 4卷 / 95期
基金：
中国国家自然科学基金;
关键词：
SUBSTITUTED; 3-HYDROXY-2-OXINDOLES; BOND FUNCTIONALIZATION; EFFICIENT SYNTHESIS; NUCLEOPHILIC-ADDITION; CONJUGATE ADDITION; 2-METHYL AZAARENES; ALPHA-ALKYLATION; METAL; CONSTRUCTION; ALDEHYDES;
D O I：
10.1039/c4ra09338k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile catalyst-free tandem sp(3) C-H functionalization/decarboxylation of 4-oxo-4H-chromene-3-carboxylic acid with 2-alkylazaarenes was developed, which can efficiently construct azaarene 2-substituted chromanones in moderate to good yields. This method proves to be efficient and innovative and the biologically significant azaarene 2-substituted chromanones can be accessed in a single step through this methodology.
引用
收藏
页码：53188 / 53191
页数：4
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  • [1] Domino reactions of 1,3-bis-silyl enol ethers with benzopyrylium triflates:: Efficient synthesis of fluorescent 6H-benzo[c]chromen-6-ones, dibenzo[c,d]chromen-6-ones, and 2,3-dihydro-1H-4,6-dioxachrysen-5-ones
    Appel, B
    Saleh, NNR
    Langer, P
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (04) : 1221 - 1236
  • [2] The bohimann-rahtz pyridine synthesis: From discovery to applications
    Bagley, Mark C.
    Glover, Christian
    Merritt, Eleanor A.
    [J]. SYNLETT, 2007, (16) : 2459 - 2482
  • [3] Catalytic enantioselective synthesis of flavanones and chromanones
    Biddle, Margaret M.
    Lin, Michael
    Scheidt, Karl A.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (13) : 3830 - +
  • [4] Highly enantioselective Cu-catalyzed conjugate additions of dialkylzinc reagents to unsaturated furanones and pyranones: Preparation of air-stable and catalytically active Cu-peptide complexes
    Brown, MK
    Degrado, SJ
    Hoveyda, AH
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (33) : 5306 - 5310
  • [5] Isolation and Immunomodulatory Effect of Homoisoflavones and Flavones from Agave sisalana Perrine ex Engelm.
    Chen, Pi Yu
    Kuo, Yuh Chi
    Chen, Chin Hui
    Kuo, Yueh Hsiung
    Lee, Ching Kuo
    [J]. MOLECULES, 2009, 14 (05) : 1789 - 1795
  • [6] New chromanone acids with antibacterial activity from Calophyllum brasiliense
    Cottiglia, F
    Dhanapal, B
    Sticher, O
    Heilmann, J
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (04): : 537 - 541
  • [7] A ROUTE TO FUNCTIONALIZED 1,5-DICARBONYL SYSTEMS VIA HETERODIENE CYCLOADDITIONS OF A 2-ACYL-2-ENOIC ACID
    COUTTS, SJ
    WALLACE, TW
    [J]. TETRAHEDRON LETTERS, 1987, 28 (43) : 5195 - 5198
  • [8] A highly enantio- and diastereoselective catalytic intramolecular stetter reaction
    de Alaniz, JR
    Rovis, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) : 6284 - 6289
  • [9] Understanding the Mechanism of the Intramolecular Stetter Reaction. A DFT Study
    Domingo, Luis R.
    Zaragoza, Ramon J.
    Saez, Jose A.
    Arno, Manuel
    [J]. MOLECULES, 2012, 17 (02): : 1335 - 1353
  • [10] The first asymmetric intramolecular Stetter reaction
    Enders, D
    Breuer, K
    Runsink, J
    Teles, JH
    [J]. HELVETICA CHIMICA ACTA, 1996, 79 (07) : 1899 - 1902
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