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Merck
  • Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines.

Expedient synthesis of tetrasubstituted pyrroles via a copper-catalyzed cascade inter-/intramolecular cyclization of 1,3-enynes carry a nitro group with amines.

Organic & biomolecular chemistry (2015-01-22)
Ganesan Bharathiraja, Mani Sengoden, Masanam Kannan, Tharmalingam Punniyamurthy
PMID25604620
ZUSAMMENFASSUNG

Various tetrasubstituted pyrroles/pyrazoles have been prepared from nitro-substituted 1,3-enynes with aromatic amines/hydrazines via a copper-catalyzed cascade aza-Michael addition, cyclization and aromatization at room temperature. This protocol is also effective for the synthesis of tetrasubstituted pyrazoles in high yields.

MATERIALIEN
Produktnummer
Marke
Produktbeschreibung
205540
Sigma-Aldrich
Kupfer(I)-Iodid, 98%
208671
Sigma-Aldrich
Bis(triphenylphosphin)palladium(II)-dichlorid, 98%
224332
Sigma-Aldrich
Kupfer(I)-chlorid, ReagentPlus®, purified, ≥99%
215554
Sigma-Aldrich
Kupfer(I)-Iodid, 99.999% trace metals basis
412740
Sigma-Aldrich
Bis(triphenylphosphin)palladium(II)-dichlorid
T84409
Sigma-Aldrich
Triphenylphosphin, ReagentPlus®, 99%
741248
Sigma-Aldrich
Bis(triphenylphosphin)palladium(II)-dichlorid
229628
Sigma-Aldrich
Kupfer(I)-chlorid, ≥99.995% trace metals basis
93094
Sigma-Aldrich
Triphenylphosphin, polymergebunden, 100-200 mesh, extent of labeling: ~1-1.5 mmol/g Capacity (Phosphor)
792063
Sigma-Aldrich
Kupfer(I)-Iodid, anhydrous, 99.995% trace metals basis
03140
Sigma-Aldrich
Kupfer(I)-Iodid, purum, ≥99.5%
651745
Sigma-Aldrich
Kupfer(I)-chlorid, AnhydroBeads™, ≥99.99% trace metals basis
93092
Sigma-Aldrich
Triphenylphosphin, ≥95.0% (GC)
939013
Copper(I) iodide ChemBeads