Issue 9, 2019

Photoinduced oxidation of an indole derivative: 2-(1′H-indol-2′-yl)-[1,5]naphthyridine

Abstract

The UV-induced oxidation of 2-(1′H-indol-2′-yl)-[1,5]naphthyridine acetonitrile solution in the presence of air leads to the formation of 2-(1,5-naphthyridin-2-yl)-4H-3,1-benzoxazin-4-one as a major product and N-(2-formylphenyl)-1,5-naphthyridine-2-carboxamide as a minor one. The probable reaction mechanisms are different for the two photoproducts and may involve both the reaction with singlet oxygen generated by the excited substrate or the reaction of the excited substrate with the ground state oxygen molecule. Electronic absorption and IR spectra indicate that both photoproducts are formed as mixtures of syn and anti-rotameric forms. The obtained results indicate an efficient and easy method for the synthesis of molecules with a benzoxazinone structure.

Graphical abstract: Photoinduced oxidation of an indole derivative: 2-(1′H-indol-2′-yl)-[1,5]naphthyridine

Supplementary files

Article information

Article type
Paper
Submitted
20 12 2018
Accepted
02 3 2019
First published
13 3 2019

Photochem. Photobiol. Sci., 2019,18, 2225-2231

Author version available

Photoinduced oxidation of an indole derivative: 2-(1′H-indol-2′-yl)-[1,5]naphthyridine

B. Golec, K. Nawara, R. P. Thummel and J. Waluk, Photochem. Photobiol. Sci., 2019, 18, 2225 DOI: 10.1039/C8PP00587G

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