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Chinese Journal of Organic Chemistry >

0 202504009 - 202504009

DOI: https://doi.org/10.6023/cjoc202504009

ARTICLE

Halogen-Bond-Promoted Direct Cross-Coupling of 2-Bromopropionitrile derivatives with Coumarins/Quinolinones: Synthesis and Transformation

  • 温吉林 ,
  • 郭鹏 ,
  • 蒲国良 ,
  • 满雪玉 ,
  • 贺春阳
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  • aGuizhou Provincial Key Laboratory of Innovation and Manufacturing for Pharmaceuticals, School of Pharmacy Zunyi Medical University Zunyi 563000

Received date: 2025-04-08

  Revised date: 2025-06-05

  Online published: 2025-07-14

Supported by

National Natural Science Foundation of China (No. 22461050, 22161054), and Science and Technology Department of Guizhou Province (No. QKHPTRC-CXTD2022-012).

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Abstract

This study reports a halogen bond-promoted cross-coupling reaction between 2-bromopropionitrile derivatives and coumarin/quinolinone compounds. The developed methodology features a simple reaction system, mild conditions, and provides target products in moderate to good yields. The cyano functional group in the obtained compounds could be efficiently converted into 2H-tetrazole derivatives under mild conditions. Comparative studies using ester analogs demonstrated significantly reduced reactivity compared to their cyano counterparts, highlighting the crucial role of the cyano group in this transformation. Preliminary cellular experiments revealed that compound 4b selectively inhibited MDA-MB-231 cells with an IC50 value of 22.8±1.3 μM, while most other compounds exhibited non-toxic or low toxicity toward both tumor cells and HL-7702 normal cells. These findings establish a foundation for further investigations into other biological activities such as antioxidant and antibacterial properties.

Key words： Halogen bond; Coumarins/quinolinones; 2-bromopropionitrile derivatives; cross-coupling reaction

Cite this article

温吉林 , 郭鹏 , 蒲国良 , 满雪玉 , 贺春阳 . Halogen-Bond-Promoted Direct Cross-Coupling of 2-Bromopropionitrile derivatives with Coumarins/Quinolinones: Synthesis and Transformation[J]. Chinese Journal of Organic Chemistry, 0 : 202504009 -202504009 . DOI: 10.6023/cjoc202504009

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