Synthesis of bis(indolyl)methanes Catalyzed by Triethylborane

被引：17
|
作者：
Garcia Merinos, J. Pablo [1 ,2 ]
Loez Ruiz, Heraclio [1 ]
Lopez, Yliana [2 ]
Rojas Lima, Susana [1 ]
机构：
[1] Univ Autonoma Estado Hidalgo, Area Acad Quim, Mineral De La Reforma 42076, Hidalgo, Mexico
[2] Univ Michoacana, Inst Invest Quim Biol, Morelia 58030, Michoacan, Mexico
来源：
LETTERS IN ORGANIC CHEMISTRY | 2015年 / 12卷 / 05期
关键词：
Arsindoline B; bis(indolyl)methanes; indole; streptindole; triethylborane; INDOLE ALKALOIDS; MILD; ACID; METABOLITE; BACTERIUM;
D O I：
10.2174/1570178612666150220225335
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Triethylborane (TEB) was found to be a mild, efficient, and acid catalyst in electrophilic substitution reaction of indoles with aldehydes compounds to afford the corresponding bis(indolyl) methanes. Vibrindole A (5) and bis(indolyl) methanes derivatives 16 and 18 were synthesized using this methodology. Compound 16 is an intermediary in the synthesis of the natural bisindoles arsindoline B (2) and streptindole (6). The structure of vibrindole A (5) was unequivocally confirmed by a single crystal X-ray diffraction analysis.
引用
收藏
页码：332 / 336
页数：5
相关论文
共 50 条
  • [1] Zeolite catalyzed synthesis of bis(indolyl) methanes
    Reddy, AV
    Ravinder, K
    Reddy, VLN
    Goud, TV
    Ravikanth, V
    Venkateswarlu, Y
    SYNTHETIC COMMUNICATIONS, 2003, 33 (21) : 3687 - 3694
  • [2] Facile Synthesis of Bis(indolyl)methanes Catalyzed by α-Chymotrypsin
    Xie, Zong-Bo
    Sun, Da-Zhao
    Jiang, Guo-Fang
    Le, Zhang-Gao
    MOLECULES, 2014, 19 (12) : 19665 - 19677
  • [3] CuBr2-catalyzed synthesis of bis(indolyl)methanes
    Mo, LP
    Ma, ZC
    Zhang, ZH
    SYNTHETIC COMMUNICATIONS, 2005, 35 (15) : 1997 - 2004
  • [4] Synthesis of bis(indolyl)methanes catalyzed by surface modified zirconia
    Nadkarni, Sharmin V.
    Gawande, Manoj B.
    Jayaram, Radha V.
    Nagarkar, Jayashree M.
    CATALYSIS COMMUNICATIONS, 2008, 9 (08) : 1728 - 1733
  • [5] A convenient synthesis of bis(indolyl)methanes catalyzed by diphosphooctadecatungstic acid
    Heravi, Majid M.
    Bakhtiari, Khadijeh
    Fatehi, Azadeh
    Bamoharram, Fatemeh F.
    CATALYSIS COMMUNICATIONS, 2008, 9 (02) : 289 - 292
  • [6] Synthesis of Bis(indolyl)methanes Catalyzed by Cyclic Phosphoric Acid
    He, Lin
    Wang, Xiangbo
    Du, Guangfen
    Dai, Bin
    Jian, Tengyue
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (05) : 988 - 994
  • [7] Efficient synthesis of bis(indolyl)methanes catalyzed by TiCl4
    Reddy, YT
    Reddy, PN
    Kumar, BS
    Rajitha, B
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2005, 44 (11): : 2393 - 2395
  • [8] p-TsOH catalyzed efficient synthesis of bis(indolyl)methanes
    Raju, B. China
    Rao, J. Madhusudana
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2008, 47 (04): : 623 - 625
  • [9] Highly efficient synthesis of bis(indolyl)methanes catalyzed by sodium tetrafluoroborate
    Kamble, Vinod Tribhuvannathji
    Bandgar, Babasaheb Pandurang
    Bavikar, Sudhir Narayanrao
    CHINESE JOURNAL OF CHEMISTRY, 2007, 25 (01) : 13 - 15
  • [10] Facile Synthesis of Bis(indolyl)methanes Catalyzed by Aluminium nitrate nonahydrate
    Amiya, Shekhar
    Deo, Pathak Devendra
    RESEARCH JOURNAL OF CHEMISTRY AND ENVIRONMENT, 2010, 14 (01): : 19 - 23
12345