Synthesis of Highly Fused Pyrano[2,3- b]pyridines via Rh(III)-Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature

Xu Han; Feng Gao; Chunpu Li; Daqing Fang; Xiong Xie; Yu Zhou; Hong Liu

doi:10.1021/acs.joc.9b03102

Synthesis of Highly Fused Pyrano[2,3- b]pyridines via Rh(III)-Catalyzed C-H Activation and Intramolecular Cascade Annulation under Room Temperature

J Org Chem. 2020 May 15;85(10):6281-6294. doi: 10.1021/acs.joc.9b03102. Epub 2020 Feb 25.

Authors

Xu Han^{1

2}, Feng Gao¹, Chunpu Li^{1

2}, Daqing Fang^{1

3}, Xiong Xie^{1

2}, Yu Zhou^{1

2}, Hong Liu^{1

2}

Affiliations

¹ State Key Laboratory of Drug Research and CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China.
² University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.
³ Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, 103 Wenhua Road, Shenhe District, Shenyang 110016, China.

PMID: 32039595
DOI: 10.1021/acs.joc.9b03102

Abstract

A facile access to the polycyclic-fused pyrano[2,3-b]pyridines has been established under room temperature via Rh(III)-catalyzed C-H bond activation and intramolecular cascade annulation. This strategy features high efficiency, unique versatility, and generality and it can occur under mild conditions in good to excellent yields. More importantly, this strategy can be extended to the late-stage functionalization of drugs possessing the CN group.

Publication types

Research Support, Non-U.S. Gov't