Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

Xiaoke Zhang; Haibo Wang; Ziwei Li; Yan Shu; Song Gan; Xuefang Zhang; Huawu Shao; Chaoyong Wang

doi:10.1021/acsomega.2c04127

Chemodivergent Synthesis of Aza-Heterocycles with a Quarternary Carbon Center via [4 + 1] Annulation between Azoalkenes and α-Bromo Carbonyl Compounds

ACS Omega. 2022 Nov 1;7(45):40963-40972. doi: 10.1021/acsomega.2c04127. eCollection 2022 Nov 15.

Authors

Xiaoke Zhang^{1

2}, Haibo Wang³, Ziwei Li¹, Yan Shu¹, Song Gan², Xuefang Zhang², Huawu Shao⁴, Chaoyong Wang¹

Affiliations

¹ Central Laboratory, Chongqing University FuLing Hospital, Chongqing 408000, P.R. China.
² Zunyi Medical University, Zunyi, Guizhou 563000, P.R. China.
³ Zhejiang Hongyuan Pharmaceutical Co., Ltd., Chem & APIs, Industrial Zone, Linhai, Taizhou 310001, Zhejiang, P.R. China.
⁴ Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 100045, P.R. China.

Abstract

An efficient [4 + 1] annulation reaction between in situ generated azoalkene intermediates and α-bromocarbonyls has been established. A series of skeletally diverse aza-heterocycles with a functionalized quaternary center were obtained in up to 89% yield under mild conditions.