A Novel One-Pot Pyrrole Synthesis via a Coupling−Isomerization−Stetter−Paal−Knorr Sequence

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 structure...

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Bibliographic Details
Published in:Organic letters 2001-10, Vol.3 (21), p.3297-3300
Main Authors: Braun, Roland U, Zeitler, Kirsten, Müller, Thomas J. J
Format: Article
Language:English
Subjects:
Combinatorial Chemistry Techniques
Crystallography, X-Ray
Isomerism
Molecular Structure
Pyrroles - chemical synthesis
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0165185