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

Article abstract of DOI:10.1246/bcsj.54.2369

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.