An unprecedented technique for the in situ generation of indolyl ortho-quinodimethanes from 2-methylindole-based methylenemalononitriles by amine-mediated remote C(sp(3) )-H deprotonation was developed. These intermediates were efficiently trapped by diverse enals to provide a rapid entry to 2,9-dihydro-1H-carbazole-3-carboxyaldehyde structures through a formal asymmetric [4+2] eliminative cycl...

3-Indolylacetic acid (IAA) is the major auxin in higher plants and plays a key role in plant growth and development. We report the rapid radiolabeling of the important plant hormone using carbon-11 (half life: 20.4 min) enabling in vivo imaging of its distribution and movement in whole plants. 3-Indolyl[1-C]acetic acid was synthesized in 2-steps: (1) reaction of gramine with [C]cyanide to give ...

an efficient and convenient protocol for synthesis of 3-hydroxy-3-indolyl-2-oxindoles and 3,3-diindolyl-2-oxindoles is presented here. the syntheses were achieved selectively under catalysis of liclo4 whereby the products were obtained purely.

The reaction of indole derivatives with cyanoacetic acid followed by treatment with DMFDMA gave the intermediate indolyl enaminonitriles (3). Further reaction with aminoguanidine yielded 5 ́-cyanomeridianin analogues (4). The same intermediate reacted with pmethoxyphenylhydrazine to give the pyrazolyl derivative (8). Treatment of (2E)-3-dimethylamino-2-(1H-indol-3-yl)-propenoate (3a) with hydrox...

Racemic 2-(5,7-dichloro-3-indolyl)propionic acid (5,7-Cl(2)-2-IPA) was synthesized from 5,7-dichloroindole-3-acetic acid by successive esterification, methoxycarbonylation, methylation, and double hydrolysis. The racemate was converted to diastereomeric esters of l-menthol; these were separated by recycling HPLC into two optically active diastereomers that were then hydrolyzed with p-TsOH to tw...

An efficient and convenient protocol for synthesis of 3-hydroxy-3-indolyl-2-oxindoles and 3,3-diindolyl-2-oxindoles is presented here. The syntheses were achieved selectively under catalysis of LiClO4 whereby the products were obtained purely.