A Novel Strategy of Ugi-4CR/Huisgen 1,3-Dipolar Synthesis of 1H-1,2,3-Triazole-Modified Peptidoimetics

Shaabani, Ahmad; Mofakham, Hamid; Hajishaabanha, Fatemeh; Mousavi Faraz, Sajjad; Pedarpour Vajargahy, Milad

doi:10.30492/ijcce.2018.29053

A Novel Strategy of Ugi-4CR/Huisgen 1,3-Dipolar Synthesis of 1H-1,2,3-Triazole-Modified Peptidoimetics

Document Type : Research Article

Authors

Faculty of Chemistry, Shahid Beheshti University, P.O Box 19396-4716, Tehran, I.R. IRAN

10.30492/ijcce.2018.29053

Abstract

In this protocol, we report a novel approach for the synthesis of a new class of heterocyclic 1H-1,2,3-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 1,3-dipolar cycloaddition reaction with an azide group in the presence of a catalytic amount of CuSO₄.5H₂O/sodium ascorbate. The copper-catalyzed Huisgen cycloaddition reactions provide such a general synthetic method, with the resulting 1,2,3-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.

Keywords

Main Subjects

Organic Chemistry

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