Construction of Substituted 1,2,3-Triazole Rings Containing Progesterone Moiety via Transition Metal-Free Cycloaddition

Abstract

In this study, a one-pot synthesis method was utilized to prepare a series of novel progesterone derivatives featuring 1,2,3-triazole rings. The condensation of progesterone with ten different aromatic aldehydes through a Claisen-Schmidt reaction gave the desired α,β-unsaturated carbonyl derivatives as intermediates, which were treated directly with benzyl azide via a metal-free [3+2] cycloaddition reaction to furnish the target derivatives 1-10 in 58-81% yields. The structure of the synthesized compounds (1-10) was characterized using FT-IR, ¹H NMR, and ¹³C NMR spectroscopy. The significant point of this work is combining two important moieties (the progesterone and 1,2,3-triazole) together to form new derivatives 1-10. This novel design of derivatives could be tested in the future to investigate its biological studies, such as anti-oxidants and anti-bacterial activities.