1174295-40-9Relevant academic research and scientific papers
Copper-Catalyzed anti-Markovnikov Hydroindolation of Terminal Alkynes: Regioselective Synthesis of Bis(indolyl)alkanes
Srivastava, Ananya,Patel, Shyam Sunder,Chandna, Nisha,Jain, Nidhi
, p. 11664 - 11670 (2016)
An efficient copper-catalyzed intermolecular hydroindolation reaction of terminal aryl alkynes to expeditiously synthesize bis(indolyl)alkanes in moderate to high yields is described. The double nucleophilic addition of two molecules of indole to one mole
The novel acid-base magnetic recyclable catalyst prepared through carbon disulfide trapping process: Applied for green, one-pot, and efficient synthesis of 2,3-dihydroquinazolin-4 (1H) -ones and bis(indolyl)methanes in large-scale
Mohammadi Metkazini, Fatemeh,Khorsandi, Zahra,Heydari, Akbar
, (2021/04/12)
Herein, a nano acid-base catalyst using magnetic core and carbamodithioic acid functional group have been synthesized and characterized. Its efficiency in the synthesis of dihydroquinazolinones and bis(indolyl)methanes derivatives was investigated. This novel metal-free catalyst exhibited significant catalytic activity in both reactions under green and mild reaction conditions (the yield obtained for the first reaction products: 82–98 % and for the second one: 61–97 %). The catalyst displayed good recyclability with no significant loss of catalytic activity after eight runs (the conversion of the eighth run was found as 83 %, the fresh catalyst conversion was 95 %). The introduced approach is attractive due to its applicability in the large-scale synthesis of important medicinal compounds.
Decarboxylative Addition of Propiolic Acids with Indoles to Synthesize Bis(indolyl)methane Derivatives with a Pd(II)/LA Catalyst
Zeng, Miao,Xue, Jing-Wen,Jiang, Hongwu,Li, Kaiwen,Chen, Yunong,Chen, Zhuqi,Yin, Guochuan
supporting information, p. 8333 - 8350 (2021/06/28)
Exploring new protocols for efficient organic synthesis is crucial for pharmaceutical developments. The present work introduces a Pd(II)/LA-catalyzed (LA: Lewis acid) decarboxylative addition reaction for the synthesis of bis(indolyl)methane derivatives. The presence of Lewis acid such as Sc(OTf)3 triggered Pd(II)-catalyzed decarboxylative addition of propiolic acids with indoles to offer the bis(indolyl)methane derivatives in moderate to good yields, whereas neither Pd(II) nor Lewis acid alone was active for this synthesis. The catalytic efficiency of Pd(OAc)2 was highly dependent on the Lewis acidity of the added Lewis acid, that is, a stronger Lewis acid provided a higher yield of the bis(indolyl)methane derivatives. Meanwhile, this Pd(II)/LA-catalyzed decarboxylative addition reaction showed good tolerance toward versatile electron-rich or-deficient substituents on the indole skeleton and on the benzyl ring of propiolic acids. The studies on the in situ 1H NMR kinetics of this Pd(II)/Sc(III) catalysis disclosed the formation of a transient vinyl-Pd(II)/Sc(III) intermediate generated by the pyrrole addition to the alkynyl-Pd(II)/Sc(III) species after decarboxylation, which was scarcely observed before.
Synthesis of Bis(indolyl)methanes through an Alkylation Reaction of Indoles with Sodium Alkoxides
Chen, Xue,Jin, Hongwei,Liu, Yunkui,Zhou, Bingwei
, (2021/12/01)
We describe an alkylation reaction of indoles with sodium alkoxides for the synthesis of bis(indolyl)methanes. 1-Tetralone proved to be an efficient hydrogen acceptor, thus avoiding the use of precious transition metals such as Ru and Ir. This reaction features transitionmetal-free conditions, uses readily available starting materials, and can be conducted on a gram scale.
BF3-grafted Fe3O4@Sucrose nanoparticles as a highly-efficient acid catalyst for syntheses of Dihydroquinazolinones (DHQZs) and Bis 3-Indolyl Methanes (BIMs)
Radfar, Iman,Miraki, Maryam Kazemi,Ghandi, Leila,Esfandiary, Naghmeh,Abbasi, Sepideh,Karimi, Meghdad,Heydari, Akbar
, (2018/07/31)
Current paper represents immobilization of sucrose on the Fe3O4 core and grafting of boron trifluoride (BF3) onto the new surface. The catalytic activity of these nanoparticles was tested in syntheses of Dihydroquinazolinones (DHQZs) and Bis (3-Indolyl) Methanes (BIMs) as two fruitful pharmaceutical structures. Acidic capacity, FT-IR, XRD, VSM, TGA and SEM–EDX tests are carried out on such novel nanoparticles (NPs). Catalyst has shown more acidic capacity per one gram of NPs than sulfonated homologue which was reported previously.
Gold-catalyzed oxidative couplings of two indoles with one aryldiazo cyanide under oxidant-free conditions
Singh, Rahulkumar Rajmani,Liu, Rai-Shung
supporting information, p. 4593 - 4596 (2017/04/28)
Gold-catalyzed oxidative couplings of two indoles and one α-cyano gold carbene to form bis(indolyl)methane derivatives are described. Two different indoles are compatible with these reactions to provide reasonable yields. A plausible mechanism is postulated to rationalize the experimental data including product distributions, D2O labeling, and the significant effects of gold catalysts and cyano groups.
Palladium(II) in electrophilic activation of aldehydes and enones: Efficient C-3 functionalization of indoles
Mohapatra, Swapna Sarita,Mukhi, Priyabrata,Mohanty, Anuradha,Pal, Satyanarayan,Sahoo, Aditya Omprakash,Das, Debjit,Roy, Sujit
supporting information, p. 5709 - 5713 (2015/09/29)
The regioselective C-3 alkylation of indoles with aldehydes and enones as electrophiles is catalyzed by a d8 late transition metal complex PdCl2(MeCN)2 at room temperature in the presence of air/moisture and in the absence
One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles
Xiang, Jiachen,Wang, Jungang,Wang, Miao,Meng, Xianggao,Wu, Anxin
supporting information, p. 4240 - 4247 (2015/04/14)
This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones. This journal is
A practical synthesis of bis(indolyl)methanes catalyzed by BF 3·Et2O
Xu, Xia-Fei,Xiong, Yan,Ling, Xue-Ge,Xie, Xi-Mi,Yuan, Jie,Zhang, Shu-Ting,Song, Zhong-Rong
supporting information, p. 406 - 410 (2014/03/21)
Practical BF3·Et2O catalyzed reactions between indoles and a series of carbonyl compounds at room temperature are described, which afford bis(indolyl)methanes with isolated yields up to 96%.
TFA-catalyzed C-N bond activation of enamides with indoles: Efficient synthesis of 3,3-bisindolylpropanoates and other bisindolylalkanes
Xu, Hai-Yan,Zi, You,Xu, Xiao-Ping,Wang, Shun-Yi,Ji, Shun-Jun
, p. 1600 - 1605 (2013/02/25)
An efficient TFA-catalyzed cleavage of C-N bonds in alkylation of indoles by tertiary enamides was described. A variety of bisindolylalkane derivatives, especially 3,3-bisindolylpropanoates, were expeditiously synthesized in good yields.
