Effect of Electron Withdrawing Group on Phenyl Boronic Acid for the Synthesis of Indole by Nickle Catalyst
DOI:
https://doi.org/10.33826/journaloms/v05i10.1Keywords:
Fischer indole synthesis, Nuclear Magnetic Resonance (NMR) Spectroscopy, Column Chromatography, Biochemical ImportanceAbstract
Indole is a major heterocyclic system that is indestructible due to its significance in biochemical importance, for example as a component of tryptophan. Indole derivatives have been identified in the literature as having a wide variety of biological characteristics and the immense potential to be used for novel treatments. One of the most proven and trustworthy methods for producing substitute indole is Fischer indole synthesis, which was developed in 1883. Since then a huge number of synthetic methods have been developed, and there a very few methods that can be used to add unsaturation at 3-position of indole. Furthermore, previous methods either required harsh reaction conditions or required the use of challenging substrates to synthesize indole by these conventional methods. In this work, we designed an approach to the synthesis of indole by using Nickle-catalyzed arylatic cyclization for alkenyl substitution at 3-position. Furthermore, the effect of electron–withdrawing groups on phenylboronic acid for the synthesis of indole by nickel catalysis was explored. A suitable substrate was synthesized by a three steps short synthesis involving N-methylation of 2-iodoaniline group at 2-position of derivatized aniline. In the presence of Ni (OAc) 2.4H2O as a catalyst, pyphos as a ligand the 2-alkinylanilid was allowed to react with electron-deficient phenylboronic acid in trifluoroethanol at 800C to give the desired 3-alkyneylindole derivatives. Reaction progress was monitored by TLC and products were purified by column chromatography. The synthesized product was characterized through techniques including infrared spectroscopy and nuclear magnetic resonance (NMR) spectroscopy. These synthesized indole derivatives can be tested to explore their potential as a biologically active agent.
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