A Novel Strategy of Ugi-۴CR/Huisgen ۱,۳-Dipolar Synthesis of ۱H-۱,۲,۳-Triazole-Modified Peptidoimetics

In this protocol, we report a novel approach for the synthesis of a new class of heterocyclic ۱H-۱,۲,۳-triazole-modified peptidomimetic compounds. The process consists of an Ugi four-component condensation reaction of amines, an isocyanide, an aldehyde and acids followed by a Huisgen ۱,۳-dipolar cycloaddition reaction with an azide group in the presence of a catalytic amount of CuSO۴.۵H۲O/sodium ascorbate. The copper-catalyzed Huisgen cycloaddition reactions provide such a general synthetic method, with the resulting ۱,۲,۳-triazoles being good peptide bond mimics. This protocol was highly efficient for structurally diverse heterocyclic molecules containing an active aldehyde group and will find applications in combinatorial chemistry, diversity-oriented synthesis, and drug discovery.

کلیدواژه ها:

۱H-۱ ، ۲ ، ۳-Triazole ، ۱ ، ۳-Dipolar cycloaddition ، Ugi four-component ، Isocyanide