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Updated: Sep 25, 2025

Functionalized Spirocyclic Heterocycle Synthesis and Cytotoxicity Assay
Published on: February 9, 2021
Cu catalyzed [4 + 2] cycloaddition for the synthesis of highly substituted 3-fluoropyridines
Yiwei Fu1, Haoyu Shi1, Shengshu Lei1
1State Key Laboratory of Bioreactor Engineering, Shanghai Key Laboratory of New Drug Design, and School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, China. hli77@ecust.edu.cn.
Abstract:
A copper catalyzed annulation-aromatization of benzyl trifluoromethyl ketimines with 3-acryloyloxazolidin-2-ones for the synthesis of 3-fluoropyridines through double C-F bond cleavages has been developed. In this approach, the annulation occurred between the in situ formed dienes from trifluoromethyl ketimines via the first C-F bond cleavage and 3-acryloyloxazolidin-2-ones. Then the aromatization afforded 3-fluoropyridines in moderate yields through the second C-F bond cleavage. The 3-fluoropyridine products could be further hydrolyzed to multi-substituted 3-pyridinecarboxylic acids.
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