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The recyclization of readily available 1-(benzoylmethylanilino)-3-imino-3H-2-cyanopyrrolizines using the DBU organic superbase, unexpectedly gave 2,2′-bipyrroles with amino, keto and cyano functional groups on one of the pyrrole rings in 83–94% yield. Previously, using the KOH/DMSO system, this recyclization led to 2,3′-bipyrroles in low yields (12–26%). This selective switching was explained by sterically...
A novel strategy for the synthesis of 4-amino-3-cyano-2,2′- and 5′-amino-4′-cyano-2,3′-bipyrroles via readily available 1-amino-3-imino-3H-pyrrolizine-2-carbonitriles has been developed. The rearrangement leading to 5′-amino-4′-cyano-2,3′-bipyrroles involves formation of the intermediate aziridine, which undergoes other side ring-opening.
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