Coupling-Isomerization-Stetter and Coupling-Isomerization-Stetter-Paal-Knorr Sequences - A Multicomponent Approach to Furans and Pyrroles
ABSTRACT 2,3,5-Trisubstituted furans 6 and 1,2,3,5-tetrasubstituted pyrroles 8 can be synthesized in good yields in a one-pot three-step three- or four-component process by a coupling-isomerization-Stetter-Paal-Knorr sequence of an electron-poor (hetero)aryl halide 1, a terminal propargyl alcohol 2,...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2004-10, Vol.2004 (14), p.2391-2406 |
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| Hauptverfasser: | , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
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| Zusammenfassung: | ABSTRACT
2,3,5-Trisubstituted furans 6 and 1,2,3,5-tetrasubstituted pyrroles 8 can be synthesized in good yields in a one-pot three-step three- or four-component process by a coupling-isomerization-Stetter-Paal-Knorr sequence of an electron-poor (hetero)aryl halide 1, a terminal propargyl alcohol 2, an aldehyde 3, and, in the case of pyrroles, a primary amine 7. All novel furans and pyrroles exhibit a strong blue fluorescence with considerable Stokes shifts. |
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| ISSN: | 0039-7881 1437-210X |
| DOI: | 10.1055/s-2004-831192 |