Synthesis of 3-Indolyl-substituted Benzoboroxole via Friedel-Crafts Reaction in Water

被引：8
|
作者：
Zhang, Huiming [1 ]
Shen, Shaochun [1 ,2 ]
Yang, Xiaodi [3 ]
Sun, Xingwen [1 ]
机构：
[1] Fudan Univ, Dept Chem, Shanghai 200433, Peoples R China
[2] Petrochem Technol, Sinopec Shanghai Res Inst, Shanghai 201208, Peoples R China
[3] Fudan Univ, Adv Mat Lab, Shanghai 200433, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 34卷 / 12期
基金：
中国国家自然科学基金;
关键词：
Friedel-Crafts reaction; 3-indole-substituted benzoboroxole; synthesis in water; CROSS-COUPLING REACTIONS; PART; DERIVATIVES; VANCOMYCIN; ENRICHMENT; PHTHALIDES; DISCOVERY; DESIGN; AGENT; ACIDS;
D O I：
10.6023/cjoc201410025
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly efficient and catalyst free approach for the synthesis of 3-indolyl-substituted benzoboroxole via Friedel-Crafts reaction in water was developed successfully using readily accessible 2-formylbenzeneboronic acid and indole as the starting material and water as solvent at room temperature. An array of desired 3-indolyl-substituted benzoboroxoles was synthesized in moderate to near quantitative yield.
引用
收藏
页码：2456 / 2461
页数：6
相关论文
共 38 条
  • [1] Discovery and structure-activity study of a novel benzoxaborole anti-inflammatory agent (AN2728) for the potential topical treatment of psoriasis and atopic dermatitis
    Akama, Tsutomu
    Baker, Stephen J.
    Zhang, Yong-Kang
    Hernandez, Vincent
    Zhou, Huchen
    Sanders, Virginia
    Freund, Yvonne
    Kimura, Richard
    Maples, Kirk R.
    Plattner, Jacob J.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (08) : 2129 - 2132
  • [2] [Anonymous], AN2690 AN2718 AN2728
  • [3] Austin P. W., 1996, CHEM ABSTR, V124
  • [4] Discovery of a new boron-containing antifungal agent, 5-fluoro-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (AN2690), for the potential treatment of onychomycosis
    Baker, Stephen J.
    Zhang, Yong-Kang
    Akama, Tsutomu
    Lau, Agnes
    Zhou, Huchen
    Hernandez, Vincent
    Mao, Weimin
    Alley, M. R. K.
    Sanders, Virginia
    Plattner, Jacob J.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (15) : 4447 - 4450
  • [5] Benzoboroxoles as efficient glycopyranoside-binding agents in physiological conditions:: Structure and selectivity of complex formation
    Berube, Marie
    Dowlut, Meenakshi
    Hall, Dennis G.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (17): : 6471 - 6479
  • [6] Synthesis and Antitumor Activity of Lycogarubin C and Lycogalic Acid
    Chen, Wang
    Hao, Huilin
    Zhang, Chenlu
    Shen, Yuemao
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (04) : 797 - 803
  • [7] ARYLBORONIC ACIDS - A MEDIUM-SIZE RING CONTAINING BORONIC ESTER GROUPS
    CUMMINGS, WM
    COX, CH
    SNYDER, HR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (06): : 1669 - &
  • [8] An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water
    Dowlut, M
    Hall, DG
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (13) : 4226 - 4227
  • [9] Bromo-boronolactonization of olefins
    Falck, JR
    Bondlela, M
    Venkataraman, SK
    Srinivas, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (21): : 7148 - 7150
  • [10] Synthesis of Indole Derivatives via Domino Reactions
    Feng, Yadong
    Zhang, Hong
    Cheng, Guolin
    Cui, Xiuling
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (08) : 1499 - 1508
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