Carbene insertion to N–H bonds of 2-aminothiazole and 2-amino-1,3,4-thiadiazole derivatives catalyzed by iron phthalocyanine

Abstract

Iron(III) phthalocyaninate decorated with crown ether substituents, [(15C5)4PcFe]Cl, efficiently catalyzed the insertion of carbene derived from ethyl diazoacetate to six amines functionalized with thiazole, thiazoline and thiadiazole heterocycles. The reactions were carried out under practical conditions using EDA:amine stoechiometric ratio with 0.05 mol% catalyst loading. Turnover numbers up to 3360 have been achieved. The aminoacid derivatives bearing heterocyclic moieties were obtained under catalytic conditions for the first time with 36–69% yields in the case of single N–H insertion products and up to 77% in the case of double N–H insertion products.