Abstract
A new highly synthetically potent series of bifunctional pyrroles, 1-vinylpyrrole-2-carbonitriles, were synthesized from readily available 1-vinylpyrrole-2-carbaldehyde oximes by two methods: (1) reaction with acetylene (KOH/DMSO, 70 °C, 10 min, yields 58–67%) and (2) reaction with acetic anhydride (90–100 °C, 5 h, yields 83–93%). Starting from 2-phenyl-1-vinylpyrrole, the one-pot synthesis of the corresponding 1-vinyl-2-carbonitrile was accomplished directly by successive treatment with a DMF/(COCl) 2 complex, NH 2OH·HCl/NaOAc, and acetic anhydride (yield 58%).
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