Abstract
3H-Pyrroles, synthesized in one-pot from ketoximes and acetylene gas in a KOH/DMSO system, undergo [4 + 2] cyclodimerization in the presence of t-BuOH (closed vessel, autogenic pressure, 140 °C, 8 h) to site- and stereoselectively afford partially hydrogenated bridgehead pyrrolo[2,3-c]pyridines in 15–60% yield. An essential feature of this synthesis is the activating effect of t-BuOH which is attributed to reversible H-bonding of the 3H-pyrroles.
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