Synthesis of 2-aminothiazoles containing 3-hydroxypyran-4-one fragment based on condensation of substituted α-arylaminoketones with thiourea

Abstract

Condensation of α-arylaminoketones bearing 3-hydroxypyran-4-one fragment with thiourea was studied. Based on considered investigation, the method for the synthesis of terarylenes with 2-aminothiazole bridge was elaborated. The presented process is the first example of construction of thiazole core starting from α-aminoketone precursor. The advantages of developed approach are easily available starting materials and convenient isolation of target products avoiding chromatographic purification. The structure of one of prepared products was confirmed by x-ray analysis. The synthetic utility of obtained 2-aminothiazoles with allomaltol substituent was demonstrated by reaction at amino and hydroxyl groups.