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Updated: Mar 15, 2026

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
A core switching strategy to pyrrolo[2,3-b]quinolines and diazocino[1,2-a]indolinones
Alan M Jones1, Stephen Patterson, Magali M Lorion
1School of Chemistry and Biomedical Sciences Research Complex, University of St Andrews, North Haugh, St Andrews, Fife, Scotland KY16 9ST, UK. a.m.jones@mmu.ac.uk njw3@st-andrews.ac.uk.
Abstract:
Two novel core-switching rearrangements to natural product-like privileged scaffolds that proceed in up to 99% yield have been developed. The deviation away from planarity of the central N-acyl urea carbonyl, caused by the structure of the medium-sized ring, dictates the exclusive reaction outcome. Proposed mechanisms and products for the reaction pathways are supported by small molecule X-ray crystallography and an isolated intermediate. Twenty-four novel rearrangement products are reported.
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