B. Trofimov, A. Ivanov, E. V. Skital'tseva
Nov 1, 2009
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Journal
Synthesis
Abstract
Hitherto inaccessible 1-vinylpyrrole-benzimidazole ensembles have been synthesized by the condensation of 1-vinyl-1 H-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 °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-(l -vinyl- I H-pyrrol-2-yl)- I H-benzimidazoles are intensely fluorescent, covering the practically important blue region (λ max 343-417 nm, Stokes shift 31-91 nm).