Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization

In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo-fused five-membered oxa- and aza-heterocycles through a formal [4+1] cyclization and subsequent acid-catalyzed intramolecular O- to N- rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late-stage modification of complex molecules and in the synthesis of a potential PD-L1 gene down-regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)-mediated sequential C─H coupling/π-allylation/dynamically favorable O-attack route.

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Publication Details

Journal
Advanced Science
Published
2024-08-29
DOI
https://doi.org/10.1002/advs.202407931
Citations
9
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
2.25

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article

Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization

Zhi‐Huan Peng, Qichen Zhan, Fengyan Gu, Zhi Zhou et al.
9 citations
Advanced Science
Cyclopropane Reaction Mechanisms
2.25
article

Ring Transformation of Cyclopropenes to Benzo‐Fused Five‐Membered Oxa‐ and Aza‐Heterocycles via a Formal [4+1] Cyclization

Zhi‐Huan Peng, Qichen Zhan, Fengyan Gu, Zhi Zhou, Tao Cao, Binyan Lin, Peng Cao, Yuanqing Wu, Mei Luo, Shijie Liu, Ning Ding
article en
9 citations

Abstract

In the context of the growing importance of heterocyclic compounds across various disciplines, numerous strategies for their construction have emerged. Exploiting the distinctive properties of cyclopropenes, this study introduces an innovative approach for the synthesis of benzo-fused five-membered oxa- and aza-heterocycles through a formal [4+1] cyclization and subsequent acid-catalyzed intramolecular O- to N- rearrangement. These transformations exhibit mild reaction conditions and a wide substrate scope. The applications in the late-stage modification of complex molecules and in the synthesis of a potential PD-L1 gene down-regulator, make this method highly appealing in related fields. Combined experimental mechanistic studies and DFT calculations demonstrate Rh(III)-mediated sequential C─H coupling/π-allylation/dynamically favorable O-attack route.

Advanced ScienceVol. 11(40)
Nanjing University of Chinese Medicine (CN), Wenzhou Medical University (CN), State Key Laboratory of Respiratory Disease (CN), Guangzhou Medical University (CN)
National Natural Science Foundation of China, Zhejiang Shuren University, Nanjing University of Chinese Medicine, Nanjing University, National Key Research and Development Program of China
Openalex Percentile: Top 12%
Cyclopropane Reaction Mechanisms
2.25
DOIOpen Access PDFOpenAlex
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