A Straightforward Synthesis of 2-(1-Vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles from 1-Vinyl-1H-pyrrole-2-carbaldehydes and o-Phenylenediamine

作者：Trofimov Boris A^*; Ivanov Andrei V; Skital'tseva Elena V; Vasil'tsov Alexander M; Ushakov Igor A; Petrushenko Konstantin B; Mikhaleva Al'bina I

来源：Synthesis, 2009, 2009(21): 3603-3610.

DOI：10.1055/s-0029-1216996

• 1-vinyl-1H-pyrrole-2-carbaldehydes
• pyrrolylbenzimidazoles
• o-phenylenediamine
• Schiff bases
• oxidative condensation

Hitherto inaccessible 1-vinylpyrrole-benzimidazole ensembles have been synthesized by the condensation of 1-vinyl-1H-pyrrole-2-carbaldehydes with o-phenylenediamine either directly or via the intermediate Schiff bases of the 1-vinyl-1H-pyrrole-2-carbaldehydes (1% TFA, DMSO, air atmosphere, 60-70 degrees C, 1 h) in yields up to 89%, the intermediate Schiff bases of exclusively E configuration being isolated in 91-98% yield (1% TFA, DMSO, r.t., 30 min). The synthesized 2-(1-vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles are intensely fluorescent, covering the practically important blue region (lambda(max) 343-417 nm, Stokes shift 31-91 nm).

• 出版日期2009-11-2