Oxidative cleavage of indoles using copper-pyridine complex.

1 January 1979

journal article
Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN

Vol. 27 (2) , 551-553
https://doi.org/10.1248/cpb.27.551

Abstract

Cu₂Cl₂-pyridine-O₂ system oxidize 2-and 3-substituted indole derivatives to form C₂-C₃ double bond cleaved products. By this reaction, 2-substituted indole (6a), 3-substituted indoles (1a-5a) and 2, 3-disubstituted indole (7a) give N-acetylanthranic acid (6b), 2-acylformanilides (1b-5b) and quinolone derivative (7b), respectively. The reaction could represent a mimic of tryptophan 2, 3-dioxygenase reaction, in which tryptophan undergoes oxidative cleavage to give N-formylkynurenin.

Keywords

TRYPTOPHAN
PYRIDINE
SUBSTITUTED INDOLE
OXIDATIVE CLEAVAGE

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