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

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作者
Olga A. Fedorova
Alina E. Saifutiarova
Elena N. Gulakova
Elena O. Guskova
Tseimur M. Aliyeu
Nikolai E. Shepel
Yuri V. Fedorov
机构
[1] A. N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences,
[2] D. Mendeleev University of Chemical Technology of Russia,undefined
来源
Photochemical & Photobiological Sciences | 2019年 / 18卷
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摘要
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.
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页码:2208 / 2215
页数:7
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