The regioselective [2 + 2] photocycloaddition reaction of 2-(3,4-dimethoxystyryl)quinoxaline in solution

Autor: Alina E. Saifutiarova, Elena N. Gulakova, Yuri V. Fedorov, Tseimur M. Aliyeu, Nikolai E. Shepel, Olga A. Fedorova, Elena O. Guskova
Rok vydání: 2019
Předmět:
Zdroj: Photochemicalphotobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 18(9)
ISSN: 1474-9092
Popis: Herein, the [2 + 2] photocycloaddition between two molecules of (E)-2-(3,4-dimethoxystyryl)-quinoxaline (1) in an acetonitrile solution to form only one cyclobutane isomer out of eleven possible isomers is described. The observed photocycloaddition reaction is reversible; thus, the studied photocycloaddition reaction can be considered as a photoreversible photochromic process. The removal of two methoxy groups from the (E)-2-(3,4-dimethoxystyryl)quinoxaline (1) structure produces compound 2, which participates only in the photoisomerization reaction. The change of the quinoxaline residue in 1 to quinoline results in the formation of compound 3, which demonstrates the regioselective oxidization electrocyclic transformation through the formation of a novel C–N bond.
Databáze: OpenAIRE