A General Approach for the Synthesis of Cyanoisopropyl Bicyclo[1.1.1]pentane (BCP) Motifs by Energy Transfer Process

Bicyclo[1.1.1]pentane (BCP) heteroaryls make up an important class of BCP derivatives in drug discovery. Herein, we report the visible-light-mediated synthesis of cyanoisopropyl BCP-heteroaryls motifs from <i>N</i>-containing heterocycles, [1.1.1]propellane, and AIBN (2,2'-azobis(isobutyronitrile)) through three-component cascade reaction. Importantly, this protocol is compatible with pyrazinones, quinoxaline-2(<i>1H</i>)-one, azauracils, quinoline derivatives, and imidazo[1,2-<i>b</i>]pyridazine, as well as various phenyl disulfide derivatives; thus, this operationally simple and general methodology could enable rapid library generation of sought-after BCP derivatives for drug development.

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Publication Details

Journal
Organic Letters
Published
2024-08-13
DOI
https://doi.org/10.1021/acs.orglett.4c02674
Citations
33
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
8.25

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article

A General Approach for the Synthesis of Cyanoisopropyl Bicyclo[1.1.1]pentane (BCP) Motifs by Energy Transfer Process

Yuxuan Zhao, Jirong Wu, Yumiao Liu, Lin Li et al.
33 citations
Organic Letters
Radical Photochemical Reactions
8.25
article

A General Approach for the Synthesis of Cyanoisopropyl Bicyclo[1.1.1]pentane (BCP) Motifs by Energy Transfer Process

Yuxuan Zhao, Jirong Wu, Yumiao Liu, Lin Li, Binbin Chen, Jiabin Shen, Qing Pang, Ge Kai, Pengfei Zhang
article en
33 citations

Abstract

Bicyclo[1.1.1]pentane (BCP) heteroaryls make up an important class of BCP derivatives in drug discovery. Herein, we report the visible-light-mediated synthesis of cyanoisopropyl BCP-heteroaryls motifs from <i>N</i>-containing heterocycles, [1.1.1]propellane, and AIBN (2,2'-azobis(isobutyronitrile)) through three-component cascade reaction. Importantly, this protocol is compatible with pyrazinones, quinoxaline-2(<i>1H</i>)-one, azauracils, quinoline derivatives, and imidazo[1,2-<i>b</i>]pyridazine, as well as various phenyl disulfide derivatives; thus, this operationally simple and general methodology could enable rapid library generation of sought-after BCP derivatives for drug development.

Organic LettersVol. 26(33)
Hangzhou Normal University (CN), Zhejiang Shuren University (CN)
Zhejiang Shuren University
Affordable and clean energy
Openalex Percentile: Top 1%
Radical Photochemical Reactions
8.25
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