Photochemical electrocyclization of the indolinylphenylethenes involving a C-N bond formation.
[reaction: see text] A novel oxidative photodehydrocyclization of indolinylphenylethenes to a polycyclic heteroaromatic cation with good yields was described. Starting from the trans derivative, the phototransformation is a multistep process. The process includes two photochemical reactions and a trans-cis isomerization reaction, followed by an 1-aza-1,3,5-hexatrienic electrocyclic reaction involving the formation of a C-N bond. The cyclized product gives the stable heteroaromatic cations from hydride elimination with oxygen from air or iodine.
Fedorova
Olga A
OA
Photochemistry Center of Russian Academy of Sciences, Novatorov str., 7a, 119421 Moscow, Russia. fedorova@photonics.ru
Fedorov
Yuri V
YV
Andryukhina
Elena N
EN
Gromov
Sergey P
SP
Alfimov
Michael V
MV
Lapouyade
René
R