51072-83-4Relevant academic research and scientific papers
Copper-catalyzed synthesis and anticancer activity evaluation of indolo[1,2-a]quinoline derivatives
Borwornpinyo, Suparerk,Chuanopparat, Nutthawat,Jearawuttanakul, Kedchin,Kanjanasirirat, Phongthon,Ngernmeesri, Paiboon,Rattanarat, Hassayaporn,Seemakhan, Sawinee,Thanetchaiyakup, Adisak
, (2021/09/14)
A simple and effective one-pot synthesis of substituted indolo[1,2-a]quinolines has been developed. The desired products were obtained in up to 98% yield when substituted 2-methyindoles were treated with 2-iodobenzaldehyde in the presence of Cs2CO3, CuI and L-proline. Our mechanistic study confirmed that the reaction sequence involved an intermolecular Knoevenagel reaction followed by an intramolecular Ullmann-type coupling reaction. Moreover, some of the synthesized compounds were found to be active against human breast (MCF-7) and colorectal (HCT-116) cancer cells with IC50 values of 27.96 μM and in the range of 6.21–46.91 μM, respectively.
An expedient route to tricyanovinylindoles and indolylmaleimides fromo-alkynylanilines utilising DMSO as a one-carbon synthon
Chakraborty, Nikita,Dahiya, Anjali,Modi, Anju,Patel, Bhisma K.,Rakshit, Amitava
supporting information, p. 6847 - 6857 (2021/08/20)
A Pd(ii)/Cu(ii) catalysed domino synthesis of tricyanovinylindoles has been achieved using DMSO as a one-carbon synthon. The reaction proceedsviathe construction of 2-aryl-3-formyl indole followed by sequential addition of malononitrile and a CN resulting
GaCl3-Catalyzed C-H Cyanation of Indoles with N-Cyanosuccinimide
Wang, Xue,Makha, Mohamed,Chen, Shu-Wei,Zheng, Huaiji,Li, Yuehui
, p. 6199 - 6206 (2019/05/24)
An efficient GaCl3-catalyzed direct cyanation of indoles and pyrroles using bench-stable electrophilic cyanating agent N-cyanosuccinimide was achieved and afforded 3-cyanoindoles and 2-cyanopyrroles in good yields and excellent regioselectivities. Notably, this protocol exhibited high reactivity for unprotected indoles and was applicable to a broad range of indole and pyrrole substrates.
Palladium-Catalyzed Late-Stage Direct Arene Cyanation
Zhao, Da,Xu, Peng,Ritter, Tobias
supporting information, p. 97 - 107 (2019/01/21)
Methods for direct benzonitrile synthesis are sparse, despite the versatility of cyano groups in organic synthesis and the importance of benzonitriles for the dye, agrochemical, and pharmaceutical industries. We report the first general late-stage aryl C–H cyanation with broad substrate scope and functional-group tolerance. The reaction is enabled by a dual-ligand combination of quinoxaline and an amino acid-derived ligand. The method is applicable to direct cyanation of several marketed small-molecule drugs, common pharmacophores, and organic dyes. Benzonitriles are some of the most versatile building blocks for organic synthesis, in particular in the pharmaceutical industry, but general methods to make them by direct C–H functionalization are unknown. In this issue of Chem, Ritter and coworkers describe a late-stage aryl C–H cyanation with broad substrate scope and functional-group tolerance, enabled by a palladium-dual-ligand catalyst system. The reaction may serve for the late-stage modification of drug candidates. Aryl nitriles constitute an important class of organic compounds that are widely found in natural products, pharmaceuticals, agricultural chemicals, dyes, and materials. Moreover, nitriles are versatile building blocks to access numerous other important molecular structure groups. However, no general method for direct aromatic C–H cyanation is known. All approaches to date require either an appropriate directing group or reactive electron-rich substrates, such as indoles, which limit their synthetic applications. Here we describe an undirected, palladium-catalyzed late-stage aryl C–H cyanation reaction for the synthesis of complex aryl nitriles that would otherwise be more challenging to produce. The wide substrate scope and good functional-group tolerance of this reaction provide direct and quick access to structural diversity for pharmaceutical and agrochemical development.
One-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions
Thanetchaiyakup, Adisak,Rattanarat, Hassayaporn,Chuanopparat, Nutthawat,Ngernmeesri, Paiboon
, p. 1014 - 1018 (2018/02/23)
A simple and efficient one-pot synthesis of substituted indolo[1,2-a]quinolines under transition-metal-free conditions has been developed. When 2-fluorobenzaldehyde was treated with substituted 2-methylindoles in the presence of Cs2CO3, the desired products were typically obtained in good to excellent yields. This reaction sequence involves a nucleophilic aromatic substitution and a Knoevenagel condensation reaction. Our mechanistic investigation revealed that both reactions could proceed as an intermolecular reaction in the first step.
Iodobenzene Dichloride/Zinc Chloride-Mediated Synthesis of N-Alkoxyindole-3-carbonitriles from 3-Alkoxyimino-2-arylalkylnitriles via Intramolecular Heterocyclization
Yun, Zhongxiang,Cheng, Ran,Sun, Jiyun,Zhang-Negrerie, Daisy,Du, Yunfei
supporting information, p. 250 - 254 (2017/11/13)
A series of N-alkoxyindole-3-carbonitriles were synthesized, under mild conditions, via intramolecular heterocyclization of the readily available 3-alkoxyimino-2-arylalkylnitriles mediated by iodobenzene dichloride/zinc chloride. The mechanism of the reaction proposes the formation of a key intermediate of nitrenium cation from a chlorination and dechlorination process facilitated by the hypervalent iodine reagent and Lewis acid respectively. (Figure presented.).
A facile and efficient synthesis of 3-cyanoindoles by a simple palladium(II)-catalyzed C─H activation of indoles
Chu, Hailiang,Guo, Mengping,Yi, Yanping,Wen, Yongju,Zhou, Lanjiang,Huang, Hongwei
, (2017/09/01)
An efficient trans-PdCl2(NH2CH2COOH)2-catalyzed direct C3-cyanation of indole C─H bonds is described. Notably, free (N─H)-indoles reacted smoothly using the procedure, and the desired product 3-cyanoindoles were obtained in good to excellent yields.
Selective access to 3-cyano-1 H -indoles, 9 H -pyrimido[4,5- b ]indoles, or 9 H -Pyrido[2,3- b ]indoles through copper-catalyzed one-pot multicomponent cascade reactions
Li, Bin,Guo, Shenghai,Zhang, Ju,Zhang, Xinying,Fan, Xuesen
, p. 5444 - 5456 (2015/06/16)
Novel and selective synthetic approaches toward indole derivatives via copper-catalyzed one-pot multicomponent cascade reactions of 1-bromo-2-(2,2-dibromovinyl)benzenes with aldehydes and aqueous ammonia are presented. Intriguingly, the concentration of a
Cyanation of indoles with benzyl cyanide as the cyanide anion surrogate
Zhang, Lianpeng,Wen, Qiaodong,Jin, Jisong,Wang, Chen,Lu, Ping,Wang, Yanguang
, p. 4236 - 4240 (2013/06/26)
A copper-mediated direct cyanation of indoles with benzyl cyanide as the cyanide anion surrogate has been achieved. The cascade reaction furnished 3-cyanoindoles under mild reaction conditions in good to excellent yields with various functional groups tolerance.
Palladium-catalyzed C(sp2) - H cyanation using tertiary amine derived isocyanide as a cyano source
Peng, Jiangling,Zhao, Jiaji,Hu, Ziwei,Liang, Dongdong,Huang, Jinbo,Zhu, Qiang
supporting information, p. 4966 - 4969,4 (2012/12/12)
An unprecedented palladium-catalyzed cyanation of aromatic C-H bonds by using tertiary amine derived isocyanide as a novel cyano source was developed. Cu(TFA)2 was used as a requisite stoichiometric oxidant. Mechanistic studies suggest that a tertiary carbon cation-based intermediate is involved following the C-N bond breakage.
