79481-87-1

Upstream product

• 83-34-1 3-Methylindole 

Downstream Products

• 83-34-1 3-Methylindole 
• 1504-06-9 3-methylindolin-2-one 

Relevant academic research and scientific papers

Electrooxidation products of methylindoles: Mechanisms and structures

Electrochemical oxidation of 1-methylindole, 2-methylindole and 3- methylindole on a platinum anode in acetonitrile containing NaClO4 has been studied. In any case no polymeric deposit on the working electrode was obtained The identification of the obtained soluble products is described and the mechanisms of formation are discussed. Analogously to the case of unsubstituted indole, electrooxidized 1-3 react through positions 2 and 3. The non polymerization of I is explained with the formation of a tetramer which is oxidized to a stable radical cation and dication without undergoing further coupling reactions.

The Reaction of Indoles in Aqueous Solution Initiated by One-electron Oxidation

By pulse or gamma radiolysis in the presence of Br-, 1-methylindole (1b) is oxidized to its radical cation (2b), which adds to (1b) to form a radical dimer (8b).Species (2b) also reacts with OH- to yield the pseudo-base, proposed to be the C2-OH adduct (4b).Identical end-product yields and spectral comparison reveal that the addition of OH. radicals to (1b) also produces (2b) and (4b) but virtually no other OH. adducts to (1b).The selectivity of OH towards the C2 position appears to apply to the other indoles as well.The neutral indolyl radicals (3) disappear both by coupling and dismutation.Discrimination between these modes is governed by the substituent.A methyl group at the C3 position favours C3-C3' coupling.Molecular oxygen adds to neutral indolyl radicals at the C3 position.The measured and estimated rates of O2 addition relate to the redox potentials of the indolyl radicals.The reaction between O2-. and the indolyl radical cation (2) produces (1) and O2.On the other hand, O2-. couples to (3) to yield C3-OOH hydroperoxides (14).The latter decompose into C2-C3 opened amides (13) with concomitant chemiluminescence.

Oxidative Cleavage Reaction of 3-Substituted Indoles Catalyzed by CuCl-Pyridine Complex under Oxygen

Oxidative cleavage of 3-methylindole using a catalytic amount of copper (II) salts with added pyridine under an oxygen atmosphere was studied.Smooth cleavage of 3-methylindole took place to give 2-formamidoacetophenone in 73-80percent yield, whereas exclusive formation of a hydrate compound derived from 3,3'-dimethyl-3,3'-bi-3H-indole resulted under anaerobic conditions.Clean oxidative cleavage of N-acetyltryptamine, methyl 3-indolylacetate, and methyl 2-acetamido-3-(3-indolyl)propionate was also achieved, constituting a mimic of tryptophan-2,3-dioxygenase.