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

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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

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Publication details

The article was received on 20 Dec 2018, accepted on 02 Mar 2019 and first published on 13 Mar 2019


Article type: Paper
DOI: 10.1039/C8PP00587G
Photochem. Photobiol. Sci., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C8PP00587G

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