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Communication | Regular issue | Vol 6, No. 2, 1977, pp.117-121
Published online, 1st January, 1970
DOI: 10.3987/R-1977-02-0117
Photochemical Ring Contraction Reactions of Quinline 1-Oxides Having Carboxylic Acid Function at the 4-Position to Indole-3-carboxaldehydes via the Corresponding Oxazepines

Chikara Kaneko* and Reiko Kitamura

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Irradiation of the N-oxide of 2-methyl- or 2-phenylquinoline 4-carboxylic acid with high-pressure mercury lamp with Pyrex filter in methanol was found to give 2-substituted indole-3-carboxaldehyde in an appreciable amount, together with carbostyril derivatives. In order to account for the formation of these indoles a plausible mechanism including benz[d]-3,1-oxazepines and 3-formyl-3H-indole-3-carboxylic acids is proposed. It was verified that the N-oxide of quinoline 4-carboxylic acid also gave indole-3-carboxaldehyde under these conditions.