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Enamine–azide [2+3]-cycloaddition as a method to introduce functional groups into fluorescent dyes

Author:
Baleeva, Nadezhda S., Zaitseva, Snizhana O., Mineev, Konstantin S., Khavroshechkina, Anastasia V., Zagudaylova, Marina B., Baranov, Mikhail S.
Source:
Tetrahedron letters 2019 v.60 no.5 pp. 456-459
ISSN:
0040-4039
Subject:
azides, chemical reactions, enamines, fluorescent dyes, moieties
Abstract:
Fluorescent dyes are a significant research tool with various applications in modern science. However, many experiments require the preparation of covalent dye conjugates, which is impossible without the presence of a functional group on the dye molecule. Unfortunately, the introduction of such groups is often a complicated task. Herein, we report a novel approach for the introduction of functional groups into fluorescent dyes, based on the [2+3]-cycloaddition reaction of “terminal” enamines with azides. The synthesis of such “terminal” enamines is carried out by the condensation of formamide acetals with a methyl group that is influenced by a strong electron withdrawing group. Thus, the proposed functionalization technique requires only the presence of a methyl group in the relevant position of the initial non-functionalized fluorescent dye.
Agid:
6290033