Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

Yan-Zhi Liu; Yao-Fu Zeng; Jiaohang Wei; Lin Xiao; Bing Shu; Jia-Lin Song; Wen-Xuan Zou; Dan-Ting Shen; Shao-Yong Chen; Yi-Chuan Zheng; Shang-Shi Zhang

doi:10.1021/acs.orglett.3c01596

Rh(III)-Catalyzed Dienylation and Cyclopropylation of 1,2,3-Benzotriazinones with Alkylidenecyclopropanes

Org Lett. 2023 Jul 21;25(28):5179-5184. doi: 10.1021/acs.orglett.3c01596. Epub 2023 Jul 6.

Authors

Affiliations

¹ Center for Drug Research and Development, Guangdong Provincial Key Laboratory of Advanced Drug Delivery, Guangdong Provincial Engineering Center of Topical Precise Drug Delivery System, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. China.
² School of Pharmaceutical Science, Hunan Provincial Key Laboratory of Tumor Microenvironment Responsive Drug Research, University of South China, Hengyang, Hunan 421001, China.
³ School of Pharmacy, Guangdong Pharmaceutical University, Guangzhou 510006, P. R. China.

PMID: 37415264
DOI: 10.1021/acs.orglett.3c01596

Abstract

Rh (III)-catalyzed dienylation and cyclopropylation of 1,2,3-benzotriazinones with alkylidenecyclopropanes (ACPs) has been achieved. Different from the previous reports of 1,2,3-benzotriazinones, the triazinone ring remained intact in this C-H bond functionlization reaction. Also, the denitrogenative cyclopropylation could also be realized by changing the reaction temperature. This protocol is featured with high E selectivity, wide substrate scope, and divergent structures of products.