Chemical Properties
Yellow Crystalline Powder
Uses
• ;Reactant for total synthesis of (±)-dibromophakellin and analogs1• ;Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine2• ;Reactant for stereoselective preparation of renieramycin G analogs3• ;Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization4• ;Reactant for Pd-catalyzed cyclization5• ;Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(
Uses
Reactant for total synthesis of (±)-dibromophakellin and analogs, synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine, stereo selective preparation of renieramycin G analogs, preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization, Pd-catalyzed cyclization and N,N-(pentane)diylbis[indolecarboxamide] and N,N-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives.
Definition
ChEBI: Indole-2-carboxylic acid is an indolyl carboxylic acid.
Synthesis
Indole-2-carboxylic acid is prepared by a two-step condensation–reductive cyclization route: starting from 1-methyl-2-nitrobenzene (1) and diethyl oxalate (2), the intermediate sodium salt of 3-(2-nitrophenyl)-2-oxopropanoic acid (3) is first obtained by condensation, which is then reduced and cyclized to give the target product indole-2-carboxylic acid (4) [1].
IC 50
NMDA Receptor; Human Endogenous Metabolite
References
[1]
Jiang, T., Liu, N., Jiang, Y.-W., Ye, P.-P., Xu, W.-M. (2017). A Practical Synthesis of Indole-2-carboxylic Acid. Organic Preparations and Procedures International, 49(5), 476–478.
https://doi.org/10.1080/00304948.2017.1374138
