A Solvent‐free, Catalyst‐free Formal [3+3] Cycloaddition Dearomatization Strategy: Towards New Fluorophores for Biomolecules Labelling. Issue 8 (15th March 2021)

• Record Type: Journal Article
• Authors: Chang, Liang; Fischer‐Durand, Nathalie; Gontard, Geoffrey; Bertrand, Benoît; Thorimbert, Serge; Dechoux, Luc
• Is Part Of: ChemSusChem. Volume 14:Issue 8(2021)
• Page Start: 1821
• Page End: 1824
• Publication Date: 2021-03-15
• Subjects: dearomatization -- fluorescent probe -- methyl coumalate -- Michael addition -- nitrogen heterocycles; Green chemistry -- Periodicals; Sustainable engineering -- Periodicals; Chemistry -- Periodicals; Chemical engineering -- Periodicals; 660
• DOI: 10.1002/cssc.202100301
• Languages: English
• ISSNs: 1864-5631

Abstract

Abstract: A general, sustainable dearomatization reaction for nitrogen‐containing heterocycles was developed. Under solvent free conditions and without catalyst, the biorenewable methyl coumalate (MC) reacted as an efficient C3 partner to convert nine types of basic aromatic rings into their pyrido[1, 2‐a] fused derivatives in good to excellent yields. The fluorescence properties of some of the products were harnessed to conjugate fluorescent tags to bovine serum albumin (BSA) and immunoglobulin G. Abstract : No solvent, no catalyst : A single solvent‐free step starting from the biobased methyl coumalate enables the dearomatization of a broad range of heterocycles affording in high yields luminescent polycyclic compounds bearing a carboxylic acid function for later grafting onto biomolecules.