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

页码：332 / 336

页数：5

共 50 条

[31] Synthesis of New Bis(Indolyl)Methanes Catalyzed by Benzylsulfamic Acid and Evaluation of Their Antimicrobial Activities
Soltani, Sara
Montazeri, Naser
Zeydi, Masoud Mohammadi
Heravi, Majid M.
PHARMACEUTICAL CHEMISTRY JOURNAL, 2020, 53 (10) : 947 - 952
[32] Palladium-catalyzed carbonylative bis(indolyl)methanes synthesis with TFBen as the CO source
Qi, Xinxin
Ai, Han-Jun
Zhang, Ning
Peng, Jin-Bao
Ying, Jun
Wu, Xiao-Feng
JOURNAL OF CATALYSIS, 2018, 362 : 74 - 77
[33] An efficient and practical synthesis of bis(indolyl)methanes catalyzed by aminosulfonic acid under ultrasound
Li, JT
Dai, HG
Xu, WZ
Li, TS
ULTRASONICS SONOCHEMISTRY, 2006, 13 (01) : 24 - 27
[34] Synthesis of New Bis(Indolyl)Methanes Catalyzed by Benzylsulfamic Acid and Evaluation of Their Antimicrobial Activities
Sara Soltani
Naser Montazeri
Masoud Mohammadi Zeydi
Majid M. Heravi
Pharmaceutical Chemistry Journal, 2020, 53 : 947 - 952
[35] Zeolite catalyzed electrophilic substitution reaction of indoles with aldehydes: synthesis of bis(indolyl)methanes
Karthik, M
Tripathi, AK
Gupta, NM
Palanichamy, M
Murugesan, V
CATALYSIS COMMUNICATIONS, 2004, 5 (07) : 371 - 375
[36] Synthesis of bis(indolyl)methanes catalyzed by acidic ionic liquid immobilized on silica (ILIS)
Hagiwara, Hisahiro
Sekifuji, Masayoshi
Hoshi, Takashi
Qiao, Kun
Yokoyama, Chiaki
SYNLETT, 2007, (08) : 1320 - 1322
[37] Synthesis of bis(indolyl) methanes catalyzed by Schiff base-Cu(II) complex
Yang, Yong Lei
Wan, Ning Ning
Wang, Wen Ping
Xie, Zheng Feng
Wang, Ji De
CHINESE CHEMICAL LETTERS, 2011, 22 (09) : 1071 - 1074
[38] PCL5 AS A MILD AND EFFICIENT CATALYST FOR THE SYNTHESIS OF BIS(INDOLYL)METHANES AND DI-BIS(INDOLYL)METHANES
Hasaninejad, Alireza
Zare, Abdolkarim
Sharghi, Hashem
Khalifeh, Reza
Zare, Ahmad Reza Moosavi
BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2008, 22 (03) : 453 - 458
[39] Highly efficient synthesis of bis(indolyl)methanes in water
Azizi, Najmodin
Torkian, Lalleh
Saidi, Mohammad R.
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 275 (1-2) : 109 - 112
[40] Green procedure for the synthesis of bis(indolyl)methanes in water
Azizi, N.
Gholibeghlo, E.
Manocheri, Z.
SCIENTIA IRANICA, 2012, 19 (03) : 574 - 578

← 1 2 3 4 5 →