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Rapid access to polysubstituted tetrahydrocarbazol-4-ones via sequential selective C−H functionalization from N-nitrosoanilines
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  • Chan Li,
  • Yanchen Yang,
  • Feifei Fang,
  • Chaoyi Liu,
  • Chunpu Li,
  • Dechuan Wang,
  • Hong Liu
Chan Li
China Pharmaceutical University
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Yanchen Yang
Shanghai Institute of Materia Medica CAS
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Feifei Fang
Shanghai Institute of Materia Medica Chinese Academy of Sciences
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Chaoyi Liu
Shanghai Institute of Materia Medica CAS
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Chunpu Li
Shanghai Institute of Materia Medica Chinese Academy of Sciences
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Dechuan Wang
China Pharmaceutical University
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Hong Liu
Shanghai Institute of Materia Medica CAS

Corresponding Author:hliu@simm.ac.cn

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Abstract

Herein, we have developed a strategy of Rh(III)-catalyzed C–H activation of N-nitrosoanilines and iodonium ylides to construct novel tetralydrocarbzol-4-one scaffolds, which provided valuable templates for sequential C-H functionalization such as alkylation, alkenyla-tion, amidation and (hetero)arylation at C5-position of tetralydrocarbzol-4-one with different coupling partners. Gram-scale synthesis and further transformation of tetralydrocarbzol-4-one derivatives to Ondansetron and its analogues demonstrated the utility of this protocol, which enabled the concise and diverse construction of biologically active molecules.
01 Mar 20231st Revision Received
02 Mar 2023Submission Checks Completed
02 Mar 2023Assigned to Editor
02 Mar 2023Review(s) Completed, Editorial Evaluation Pending
02 Mar 2023Reviewer(s) Assigned
23 Mar 2023Editorial Decision: Accept