[reaction: see text]. 1,2,3,5-tetrasubstituted pyrroles can be synthesized in good yields in a one-pot, three-step, four-component process by a coupling-isomerization-Stetter reaction-Paal-Knorr sequence of an electron-poor (hetero)aryl halide, a terminal propargyl alcohol, an aldehyde, and a primary amine. The structures of the 1,4-diketone 4f and the pyrrole 6b were additionally supported by X-ray structure analyses.
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Braun et al. (2001) studied this question.
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