1344663-42-8Relevant articles and documents
Synthesis of 1-vinylpyrrole-imidazole alkaloids
Belyaeva, Kseniya V.,Andriyankova, Ludmila V.,Nikitina, Lina P.,Ivanov, Andrei V.,Afonin, Andrei V.,Ushakov, Igor A.,Malkina, Anastasiya G.,Mikhaleva, Albina I.,Trofimov, Boris A.
experimental part, p. 2843 - 2847 (2011/10/18)
The reaction between 1-methylimidazole, cyano(phenyl)acetylene, and 1-vinylpyrrole-2-carbaldehydes (MeCN, 20-25 C) stereoselectively gives 1-vinylpyrrole-imidazole ensembles with a (Z,Z)-bis(2-cyano-1-phenylvinyl)oxy function in up to 45% yield. Unlike recently reported three-component reaction between imidazoles, electron-deficient acetylenes, and aldehydes affording 1:1:1 adducts, in this case two molecules of acetylene are involved to deliver 1:2:1 adducts thus representing a novel functionalizaton of the pyrrole-imidazole alkaloid scaffold. The initial zwitterion generated from imidazole and cyano(phenyl)acetylene is thought to be transformed into a carbene, which reacts with pyrrole-2-carbaldehyde. Two subsequent rearrangements of the 1:1:1 adduct furnish the intermediate pyrrole-imidazole ensemble, which in its enol form adds to second molecule of cyano(phenyl)acetylene to yield the final products, functionalized pyrrole-imidazole alkaloids. Georg Thieme Verlag Stuttgart - New York.
