Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid

被引：2
|
作者：
He, Lin [1 ,2 ]
Wang, Xiangbo [1 ,2 ]
Du, Guangfen [1 ,2 ]
Dai, Bin [1 ,2 ]
Jian, Tengyue [3 ]
机构：
[1] Shihezi Univ, Key Lab Green Proc Chem Engn Xinjiang Bingtuan, Shihezi 832000, Peoples R China
[2] Shihezi Univ, Sch Chem & Chem Engn, Shihezi 832000, Peoples R China
[3] Chinese Acad Sci, Natl Lab Mol Sci, Key Lab Mol Recognit & Funct, Inst Chem, Beijing 100190, Peoples R China
来源：
CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 33卷 / 05期
关键词：
indole; aldehyde; ketone; cyclic phosphoric acid; bis(indolyl)methanes; ROOM-TEMPERATURE; FACILE SYNTHESIS; SULFURIC-ACID; ONE-POT; INDOLES; EFFICIENT; MILD; DIINDOLYLMETHANES; METABOLITE; ALDEHYDES;
D O I：
10.6023/cjoc201212006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclic phosphoric acid was found to be an efficient Bronsted acid catalyst for the electrophilic substitution reaction of indole with aldehydes or ketones in dichloromethane to afford the corresponding bis(indolyl)methanes in excellent yields at room temperature. The influence of catalyst structure, catalyst loading and reaction media was investigated, the optimal reaction conditions were obtained and a possible mechanism for the reaction was proposed. The simple procedure, mild reaction conditions, low catalyst loading, high yield and environmentally friendly organocatalyst provide a valuable approach for the preparation of bis(indolyl)methanes.
引用
收藏
页码：988 / 994
页数：7
相关论文
共 36 条
  • [1] Ammonium chloride catalyzed one-pot diindolylmethanes under solvent-free synthesis of conditions
    Azizian, Javad
    Teimouri, Fatemeh
    Mohammadizadeh, Mohammad Reza
    [J]. CATALYSIS COMMUNICATIONS, 2007, 8 (07) : 1117 - 1121
  • [2] A convenient method of synthesis of bis-indolylmethanes:: Indium trichloride catalyzed reactions of indole with aldehydes and Schiff's bases.
    Babu, G
    Sridhar, N
    Perumal, PT
    [J]. SYNTHETIC COMMUNICATIONS, 2000, 30 (09) : 1609 - 1614
  • [3] Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions
    Bandgar, BP
    Shaikh, KA
    [J]. TETRAHEDRON LETTERS, 2003, 44 (09) : 1959 - 1961
  • [4] VIBRINDOLE-A, A METABOLITE OF THE MARINE BACTERIUM, VIBRIO-PARAHAEMOLYTICUS, ISOLATED FROM THE TOXIC MUCUS OF THE BOXFISH OSTRACION-CUBICUS
    BELL, R
    CARMELI, S
    SAR, N
    [J]. JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1994, 57 (11): : 1587 - 1590
  • [5] Lewis acid-catalyzed reactions in protic media. Lanthanide-catalyzed reactions of indoles with aldehydes or ketones
    Chen, DP
    Yu, LB
    Wang, PG
    [J]. TETRAHEDRON LETTERS, 1996, 37 (26) : 4467 - 4470
  • [6] 6-BROMOTRYPTAMINE DERIVATIVES FROM THE GULF OF CALIFORNIA TUNICATE DIDEMNUM-CANDIDUM
    FAHY, E
    POTTS, BCM
    FAULKNER, DJ
    SMITH, K
    [J]. JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02): : 564 - 569
  • [7] Indolyl carboxylic acids by condensation of indoles with α-keto acids
    Garbe, TR
    Kobayashi, M
    Shimizu, N
    Takesue, N
    Ozawa, M
    Yukawa, H
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (05): : 596 - 598
  • [8] Facile and Mild Synthesis of bis(3-Indolyl)methanes
    Ghorbani-Vaghei, R.
    Malaekehpoor, S. M.
    [J]. ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2010, 42 (02) : 175 - 182
  • [9] A practical and efficient synthesis of bis(indolyl)methanes in water, and synthesis of di-, tri-, and tetra(bis-indolyl)methanes under thermal conditions catalyzed by oxalic acid dihydrate
    Ghorbani-Vaghei, Ramin
    Veisi, Hojat
    Keypour, Hassan
    Dehghani-Firouzabadi, Ahmad Ali
    [J]. MOLECULAR DIVERSITY, 2010, 14 (01) : 87 - 96
  • [10] Research Progress of Synthesis of Bis(indolyl)methanes
    Gong, Haiwei
    Xie, Zhengfeng
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (07) : 1195 - 1207
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