Rh(III)-Catalyzed C-H Activation and [4+1+1] Sequential Cyclization Cascade to Give Highly Fused Indano[1,2- b]azirines

Fuqiang Zheng; Jianhui Zhou; Feifei Fang; Jiyuan Li; Jing Wang; Miao Zheng; Hong Liu; Yungen Xu; Yu Zhou

doi:10.1021/acs.orglett.2c02070

Rh(III)-Catalyzed C-H Activation and [4+1+1] Sequential Cyclization Cascade to Give Highly Fused Indano[1,2- b]azirines

Org Lett. 2022 Aug 12;24(31):5688-5692. doi: 10.1021/acs.orglett.2c02070. Epub 2022 Aug 3.

Authors

Fuqiang Zheng^{1

2}, Jianhui Zhou², Feifei Fang², Jiyuan Li², Jing Wang², Miao Zheng², Hong Liu^{1

2

3}, Yungen Xu¹, Yu Zhou^{2

3}

Affiliations

¹ Department of Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, China.
² State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai 201203, China.
³ School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China.

PMID: 35921178
DOI: 10.1021/acs.orglett.2c02070

Abstract

A Rh(III)-catalyzed C-H activation of α-keto oximes and a cyclization cascade with diazo compounds were developed to construct the highly fused indano[1,2-b]azirine frameworks in good yields with a broad range of substrates under mild reaction conditions. More intriguingly, a [4+1+1] sequential annulation cascade is demonstrated for the first time in this reaction and opened a new reaction mode for α-keto oximes. These fused indano[1,2-b]azirine derivatives could also be further transformed into intriguing privileged drug scaffolds.