A New Synthetic Strategy for the Synthesis of 2-amino-6-R-[1,3]thiazolo[5,4-b]pyridines
Abstract
Derivatives of 1,3-thiazolopyridine are synthetically available compounds that are actively studied due to their potential antibacterial and anti-tumor activity.
Recently [1,3]thiazolo[5,4-b]pyridine alkaloid, janthinedine A, was isolated from Taxus wallichiana var. chinensis (Pilger) Florin as a secondary metabolite, which demonstrated high antimicrobial and antifungal activities.
The article discusses the new approach to the synthesis of 2-aminothiazolo[5,4-b]pyridine derivatives that is based on the nucleophilic substitution in 2-chloro-3-nitropyridines by the action of KSH with simultaneous reduction of nitro group. 3-Aminopyridine-2(1H)-thiones obtained in this way react with cyanogen bromide in anhydrous MeOH to form the target products in good yields. According to LCMS data, the purity of the target products obtained by the proposed method exceeds 95%.
The structures of the compounds were proved using 1H NMR, 13C NMR and mass-spectra.
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