- Lanthanide triflates catalyzed reactions of imines with indole in protic media
-
Lanthanide triflates Ln(OTf)3 were found to catalyze the electrophilic substitution reactions of indole with a variety of imines in protic media, affording predominately secondary indolyl amines as well as bisindolyl methanes as by-products.
- Xie, Wenhua,Bloomfield, Karen M.,Jin, Yafei,Dolney, Nicole Y.,Wang, Peng George
-
-
Read Online
- Triarylmethyl Cation-Catalyzed Three-Component Coupling for the Synthesis of Unsymmetrical Bisindolylmethanes
-
An efficient synthesis of unsymmetrical bisindolylmethanes has been accomplished using triarylmethyl cations to catalyze the reaction of N-arylimines with two different indoles. Optimization of the organocatalyst by tuning cation stability allows for excellent single addition selectivity when coupled with p-nitrophenyl imines. The optimal catalyst is commercially available, and the reaction minimizes waste and environmental impact by employing a one-to-one ratio of starting materials. The intermediates can be isolated or used in situ in a one-pot two-step reaction to generate unsymmetrical bisindolylmethanes in high yields. The reaction tolerates a broad range of imines with the highest yields observed for electron-poor and neutral imines. A wide range of indole nucleophiles are also successfully employed allowing for the creation of a large variety of unsymmetrical bisindolylmethanes.
- Bardelski, Kevin,Brindle, Cheyenne S.,Chen, Zhenghua,Guarino-Hotz, Melissa,Jones, Vanessa A.,Lucas, Kelly,Patterson, William J.
-
supporting information
p. 6737 - 6742
(2021/12/31)
-
- Natural Products for Drug Discovery: Discovery of Gramines as Novel Agents against a Plant Virus
-
Plant viral diseases seriously affect crop yield and quality. The natural product gramine (1) and its simple structural analogues 2-35 were synthesized from indoles, amines, and aldehydes in one step. The antiviral effects of these alkaloids were evaluated systematically. Most of these compounds were found to have higher antiviral effects than commercial ribavirin for the first time. Especially compounds 22, 30, and 31 exhibited significantly higher effects than ningnanmycin, thereby emerging as novel antiviral leads for further optimization. The preliminary implementation indicated that these compounds likely inhibit the assembly of tobacco mosaic virus (TMV) by cross-linking TMV capsid protein. Gramine analogues were also found to have broad-spectrum fungicidal effects. Although gramine has been reported to have influence on germination and development of Erysiphe graminis, these compounds displayed no fungicidal effects against Blumeria graminis f. sp. tritici on wheat in our test. Some of these compounds also exhibited certain insecticidal activities.
- Lu, Aidang,Wang, Tienan,Hui, Hao,Wei, Xiaoye,Cui, Weihao,Zhou, Chunlv,Li, Hongyan,Wang, Ziwen,Guo, Jincheng,Ma, Dejun,Wang, Qingmin
-
p. 2148 - 2156
(2019/03/08)
-
- A distinct novel approach for the synthesis of 3-indolyl-methanamines starting from indoles, aldehydes and nitrobenzenes in water
-
3-Indolyl-methanamines have efficiently been synthesized by the treatment of indoles with aldehydes and nitrobenzenes using indium in aqueous HCl at room temperature. The products are formed in excellent yields (91-98%) within a short period of time (30-45 min). Bisindolyl methanes have not been obtained under the present reaction conditions. The Royal Society of Chemistry 2013.
- Das, Biswanath,Kumar, Jayprakash Narayan,Kumar, Avula Satya,Satyalakshmi, Gandham,Shinde, Digambar Balaji
-
p. 14308 - 14311
(2013/09/02)
-
- Dy(OTf)3 in ionic liquid: An efficient catalytic system for reactions of indole with aldehydes/ketones or imines
-
Dy(OTf)3 immobilized in ionic liquids was found to be an efficient catalytic system for the reactions of indole with aldehydes/ketones or imines. Enhanced activity was observed. The use of ionic liquids as the reaction media allows facile separ
- Mi, Xueling,Luo, Sanzhong,He, Jiaqi,Cheng, Jin-Pei
-
p. 4567 - 4570
(2007/10/03)
-