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Novel Sulfur Containing 1,4-Disubstituted-1,2,3-Triazoles Catalyzed by CuI in Water
Published: 31 October 2013 by MDPI in The 17th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis
Abstract: 1,2,3-Triazole derivatives have received a great deal of attention because of their wide range of applications and biological activities such as anti-HIV and antimicrobial agents. The most popular method for the construction of 1,2,3-triazole frameworks is the 1,3-dipolar Huisgen cycloaddition reaction of azides with alkynes. However, a mixture of the 1,4- and 1,5-regioisomers may result, and efforts have been made to selectively gain one of the regioisomers. Huisgen reaction using amine or alcohol as one of the reactants to afford nitrogen and oxygen containing 1,2,3-triazoles have been already reported, but in the case of sulfur containing triazoles, it is desirable to develop a new, convenient and regiocontrolled synthetic approach. In this work, we have presented a three component reaction of thiols, propargyl bromide and organic azides using copper iodide catalyst under aerobic conditions in water to afford the corresponding sulfur containing1,4-disubstituted-1,2,3-triazoles. Our method has the advantages of operational simplicity, mild reaction conditions, use of ambient temperature, no moisture or air sensitivity, 1,4-regioselectivity and simple reaction work-up.
Keywords: 1,2,3-triazoles; thiols; copper(I) iodide; propargyl bromide; termina alkynes