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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
939013
Copper(I) iodide ChemBeads
208671
Sigma-Aldrich
Bis(triphenylphosphin)palladium(II)-dichlorid, 98%
205540
Sigma-Aldrich
Kupfer(I)-Iodid, 98%
224332
Sigma-Aldrich
Kupfer(I)-chlorid, ReagentPlus®, purified, ≥99%
T84409
Sigma-Aldrich
Triphenylphosphin, ReagentPlus®, 99%
215554
Sigma-Aldrich
Kupfer(I)-Iodid, 99.999% trace metals basis
412740
Sigma-Aldrich
Bis(triphenylphosphin)palladium(II)-dichlorid
741248
Sigma-Aldrich
Bis(triphenylphosphin)palladium(II)-dichlorid
229628
Sigma-Aldrich
Kupfer(I)-chlorid, ≥99.995% trace metals basis
03140
Sigma-Aldrich
Kupfer(I)-Iodid, purum, ≥99.5%
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
651745
Sigma-Aldrich
Kupfer(I)-chlorid, AnhydroBeads™, ≥99.99% trace metals basis
93092
Sigma-Aldrich
Triphenylphosphin, ≥95.0% (GC)