Author:
Adly Mina E.,Mahmoud Amr M.,El-Nassan Hala B.
Abstract
AbstractIn this study, a new green method was developed for the synthesis of bis(indolyl)methane derivatives using electrochemical bisarylation reaction in deep eutectic solvents as a green alternative to traditional solvents and electrolytes. The effects of varying time, current, type of solvent and material of electrodes were all studied. The optimum reaction conditions involved the use of ethylene glycol/choline chloride with a ratio of 2:1 at 80 °C for 45 min. Graphite and platinum were used as cathode and anode, respectively. The newly developed method offered many advantages such as using mild reaction conditions, short reaction time and affording high product yields with a wide range of substituted aromatic aldehydes bearing electron donating or electron withdrawing substituents. In addition, the electrochemical method proved to be more effective than heating in deep eutectic solvents and afforded higher yields of products in shorter reaction time. The mechanism of the electrochemical reaction was proposed and confirmed using the cyclic voltammetry study.
Publisher
Springer Science and Business Media LLC
Reference84 articles.
1. Imran S, Taha M, Ismail N. A review of bisindolylmethane as an important scaffold for drug discovery. Curr Med Chem. 2015;22:4412–33.
2. Shiri M, Zolfigol MA, Kruger HG, Tanbakouchian Z. Bis- and trisindolylmethanes (BIMs and TIMs). Chem Rev. 2010;110:2250–93.
3. Praveen PJ, Parameswaran PS, Majik MS. Bis(indolyl)methane alkaloids: isolation, bioactivity, and syntheses. Synthesis. 2015;47:1827–37.
4. Fang SY, Chen SY, Chen YY, Kuo TJ, Wen ZH, Chen YH, et al. Natural indoles from the bacterium Pseudovibrio denitrificans P81 isolated from a marine sponge. Aaptos Species Nat Prod Commun. 2021;16:1–6.
5. Marrelli M, Cachet X, Conforti F, Sirianni R, Chimento A, Pezzi V, et al. Synthesis of a new bis(indolyl)methane that inhibits growth and induces apoptosis in human prostate cancer cells. Nat Prod Res. 2013;27:2039–45.