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Journal Articles Journal of Organic Chemistry Year : 2022

Photoisomerization of Arylidene Heterocycles: Toward the Formation of Fused Heterocyclic Quinolines

Abstract

We report herein the photoinduced isomerization of a series of arylidene heterocycles 1. The photoreaction mechanism was investigated by a combined UV–vis/photo-NMR spectroscopic study, and we showed that Ar-TZDs exhibit a positive P-type photochromism, which limits their isomerization efficiency. By exploring the solvatochromism in a series of solvents, the conditions favoring the conversion toward one or the other stereoisomer have been studied, in particular by choosing the appropriate wavelengths. Finally, the extension of this photoisomerization study was proposed with a convenient preparation of various fused heterocyclic quinolines in good overall yields.
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Dates and versions

hal-03826852 , version 1 (24-10-2022)

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Elodie Cortelazzo-Polisini, Michel Boisbrun, Axel Hans Gansmüller, Corinne Comoy. Photoisomerization of Arylidene Heterocycles: Toward the Formation of Fused Heterocyclic Quinolines. Journal of Organic Chemistry, 2022, 87 (15), pp.9699-9713. ⟨10.1021/acs.joc.2c00748⟩. ⟨hal-03826852⟩
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