A Cascade Synthesis of Furo-Pyrrolo-Pyridines via Pd(II)-Catalyzed Dual N-H/C Annulative-Cyclization

Chemistry. 2024 Nov 18:e202403470. doi: 10.1002/chem.202403470. Online ahead of print.

Abstract

A Pd(II)-catalyzed non-template synthesis of furo[2,3-b]pyrrolo[2,3-d]pyridines from β-ketodinitriles and buta-1,3-diynes has been accomplished via dual annulative cyclization. The participation of both the nitrile (-CN) groups led to the concurrent construction of three heterocycles viz. furan, pyrrole, and pyridine forming C-C, C=C, C-O, C-N, and C=N bonds in one pot. The synthetic utility of the protocol was further demonstrated through a few post-synthetic manipulations.

Keywords: Annulations; Furo-pyrrolo-pyridines; Fused heterocycles; Nitrile-triggered; Pd(II)-catalyst.