Related Experiment Video
Updated: Oct 26, 2026

Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Scaffold Hopping of Pyrimidines into 2-Acylpyrroles
Enxian Li1, Cong Lv1, Shunyao Huang1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education College of Chemistry, Sichuan University, Chengdu610064, P. R. China.
Abstract:
A practical skeletal-editing strategy was developed for the conversion of 4-substituted pyrimidines into 2-acyl-5-arylpyrroles. The transformation directly converts a six-membered, electron-deficient pyrimidine into a five-membered azole while simultaneously installing an acyl group. The reaction sequence involves pyrimidine activation, ring-opening, fragmentation, and ring reconstruction. Central to this strategy is the controlled generation of pyrimidine-derived vinamidinium salts as open-chain A4 synthons, which are then intercepted by α-bromoketones as functionalized annulation reagents. The developed scaffold-hopping method can be applied for late-stage modification of pyrimidine-containing bioactive or pharmaceutical molecules.
Related Concept Videos
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
Cycloaddition Reactions: Overview
Criteria for Aromaticity and the Hückel 4n + 2 Rule
For the first time, Eric Hückel, a German chemical physicist, derived a set of structural features for a compound to be classified as aromatic. This is now known as Hückel’s rule or the 4n + 2 rule.
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

