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Updated: Jun 12, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
One-pot synthesis of functionalized dihydropyridin-2-ones via carbene-catalyzed base-controlled [3+3] annulation
Zhan-Yong Wang1, Guoyang Ma2, Yaoyao Xu1
1School of Pharmacy, Xinxiang University, Xinxiang 453003, China. xiaran3324@163.com.
Abstract:
Herein, we have described a novel organocatalytic approach to access biologically important dihydropyridin-2-ones in a one-pot way with generally high yields (up to 99%) and excellent enantioselectivities (up to 99% ee). This reaction proceeded via a new dual activation mode, including in situ-generated α,β-unsaturated acylazoliums and 4-dimethylaminopyridinium salts that underwent a Michael addition/1,4-H migration/lactamization sequence. The base-triggered 4-dimethylaminopyridinium ylide formation pathway over the competing substitution reaction pathway of vicinal haloamines is noteworthy.
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