A photochemical electrocyclization of the benzothiazolylphenylethenes involving a C-N bond formation

O. A. Fedorova (1) , E. N. Gulakova (1) , Y. V. Fedoroy (1) , I. E. Lobazova (1) , M. V. Alfirnov (1) , Gediminas Jonusauskas (2)

1 Photochemistry Center [Moscou]
2 CPMOH - Centre de physique moléculaire optique et hertzienne

A novel oxidative photodehydrocyclization of benzothiazolylphenylethenes to a polycyclic heteroaromatic cations with good yields was described. Starting from the trans-derivative, the phototransformation is a multistep process. It includes two photochemical reactions, a trans-cis-isomerization reaction followed by an 1-aza-1,3,5-hexatrienic electrocyclic reaction involving the formation of CN bond. The cyclized product gives the stable heteroaromatic cations from hydride elimination with oxygen from air.

Mots clés: Electrocyclic reaction; Photocyclization; 2-Styrybenzothiazoles; Crown ethers; Benzothiazolo[3; 2-a]quinolines

Domaines: Physique [physics]; Optique [physics.optics]

O. A. Fedorova, E. N. Gulakova, Y. V. Fedoroy, I. E. Lobazova, M. V. Alfirnov, et al.. A photochemical electrocyclization of the benzothiazolylphenylethenes involving a C-N bond formation. Journal of Photochemistry and Photobiology A: Chemistry, 2008, 196 (2-3), pp.239-245. ⟨10.1016/j.jphotochem.2007.07.036⟩. ⟨hal-01552916⟩