Three-step synthesis of an annulated β-carboline via palladium catalysis.

Autor: Mulcahy SP; Providence College, Department of Chemistry and Biochemistry, 1 Cunningham Square, Providence, RI 02908, USA., Varelas JG; Providence College, Department of Chemistry and Biochemistry, 1 Cunningham Square, Providence, RI 02908, USA.
Jazyk: angličtina
Zdroj: Tetrahedron letters [Tetrahedron Lett] 2013 Nov 27; Vol. 54 (48).
DOI: 10.1016/j.tetlet.2013.09.108
Abstrakt: The synthesis of β-carbolines is a mature field, yet new methods are desirable to introduce new functionality onto the core scaffold. We describe the incorporation of an additional fused ring onto the β-carboline via a novel palladium-catalyzed, one-pot Sonogashira coupling/intramolecular [2+2+2] cyclization. This method generates three rings in one flask and produces an annulated β-carboline in 80% yield. A preliminary mechanistic study into the sequence of events is described, which confirms an unprecedented catalytic role for palladium.
Databáze: MEDLINE