Rhodium(III)-Catalyzed Oxidative [3 + 2] Annulation of 2-Acetyl-1-arylhydrazines with Maleimides: Synthesis of Pyrrolo[3,4- b]indole-1,3-diones

He Li; Sheng Zhang; Xiujuan Feng; Xiaoqiang Yu; Yoshinori Yamamoto; Ming Bao

doi:10.1021/acs.orglett.9b03107

Rhodium(III)-Catalyzed Oxidative [3 + 2] Annulation of 2-Acetyl-1-arylhydrazines with Maleimides: Synthesis of Pyrrolo[3,4- b]indole-1,3-diones

Org Lett. 2019 Nov 1;21(21):8563-8567. doi: 10.1021/acs.orglett.9b03107. Epub 2019 Oct 16.

Authors

He Li¹, Sheng Zhang¹, Xiujuan Feng¹, Xiaoqiang Yu¹, Yoshinori Yamamoto^{1

2

3}, Ming Bao¹

Affiliations

¹ State Key Laboratory of Fine Chemicals , Dalian University of Technology , Dalian 116023 , China.
² Department of Chemistry, Graduate School of Science , Tohoku University , Sendai 980-8578 , Japan.
³ Research Organization of Science and Technology , Ritsumeikan University , Kusatsu, Shiga 525-8577 , Japan.

PMID: 31617727
DOI: 10.1021/acs.orglett.9b03107

Abstract

A rhodium-catalyzed oxidative [3 + 2] annulation of 2-acetyl-1-phenylhydrazines with maleimides was accomplished using AgNTf₂ and Ag₂CO₃ as additive and oxidant, respectively. A variety of 2-acetyl-1-phenylhydrazines with maleimides were converted into pyrrolo[3,4-b]indole-1,3-diones in satisfactory to excellent yields. Synthetically useful functional groups, such as halogen atoms (F, Cl, Br, and I), ester, cyano, and nitro, remained intact during tandem C-H activation and annulation reactions.