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

TETRAHEDRON LETTERS

卷:54

Article

Mulcahy, Seann P.¹  Varelas, Jonathan G.¹ 

[1] Providence Coll, Dept Chem & Biochem, Providence, RI 02918 USA

关键词: beta-Carboline;    Cyclotrimerization;    Sonogashira coupling;    Palladium catalysis;    Heteroannulation;   

DOI  :  10.1016/j.tetlet.2013.09.108

来源: Elsevier

【 摘 要 】

The synthesis of beta-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 p-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 beta-carboline in 80% yield. A preliminary mechanistic study into the sequence of events is described, which confirms an unprecedented catalytic role for palladium. (C) 2013 Elsevier Ltd. All rights reserved.

【 授权许可】

Free