Versatile transamination in quinonediimine chemistry: Towards a novel class of water soluble UV/violet chromophores. Issue 38 (19th September 2019)

• Record Type: Journal Article
• Authors: Chen, Zhongrui; Bert, Maxime; Pascal, Simon; Canard, Gabriel; Siri, Olivier
• Is Part Of: Tetrahedron letters. Volume 60:Issue 38(2019)
• Publication Date: 2019-09-19
• Subjects: Transamination -- 2, 5-Diaminobenzoquinone diimine -- Quinoxaline -- Fluorophore -- Blue-green fluorescence; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2019.151024
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Transamination reactions on quinonediimines (QDI) with polyamines is reported. The use of ethylenediamine afforded a quinoxaline derivative. Transamination with tetraamine gave a novel class of water soluble UV absorbers. Abstract: The transamination reaction of 2, 5-diaminobenzoquinonediimine (QDI) with ethylenediamine gave fluorescent 1, 2, 3, 4-tetrahydropyrazino[2, 3- g ]quinoxaline (1 ). When the same reaction was carried out with N, N' -bis(aminoethyl)-1, 3-propanediamine, a novel cationic quinoxalinium species (2 ) was isolated, which can be further condensed with p -cyanobenzaldehyde to afford a benzimidazolo-fused quinoxaline dye (3 ) that is a water-soluble fluorophore in the UV–visible range.