1332941-38-4Relevant academic research and scientific papers
Efficient syntheses of 1,2,3-triazoloamide derivatives using solid- and solution-phase synthetic approaches
Lee, Doohyun,Kim, Daehun,Lee, Seungyeon,Kim, Taegeum,Kim, Joobin,Kim, Sohee,Liu, Kwang-Hyeon,Lee, Sangkyu,Bae, Jong-Sup,Song, Kyung-Sik,Cho, Chang-Woo,Son, Youn Kyung,Baek, Dong Jae,Lee, Taeho
, p. 19984 - 20013 (2015/12/23)
Efficient synthetic routes for the preparation of secondary and tertiary 1,2,3-triazoloamide derivatives were developed. A secondary α-1,2,3-triazoloamide library was constructed and expanded by a previously developed solid-phase synthetic route and a tertiary 1,2,3-triazoloamide library was constructed by a parallel solution-phase synthetic route. The synthetic routes rely on amide formation with secondary amines and chloro-acid chlorides; SN2 reaction with sodium azide; and the selective [3 + 2] Hüisgen cycloaddition with appropriate terminal alkynes. The target secondary and tertiary 1,2,3-triazoloamide derivatives were obtained with three-diversity points in excellent overall yields and purities using the reported solid- and solution-phase synthetic routes, respectively.
Synthesis of 5-Iodo-1,2,3-triazoles from organic azides and terminal alkynes: Ligand acceleration effect, substrate scope, and mechanistic insights
Barsoum, David N.,Brassard, Christopher J.,Deeb, Jason H. A.,Okashah, Najeah,Sreenath, Kesavapillai,Simmons, J.Tyler,Zhu, Lei
, p. 2372 - 2386 (2013/09/23)
An improved method has been developed for the preparation of 5-iodo-1,2,3-triazoles directly from organic azides and terminal alkynes by a reaction mediated by copper(I) and iodinating agents generated in situ. The major methodological advance of the current procedure is that it provides a high conversion and good iodo/proto selectivity with a broad range of substrates without using an excess of the alkyne, which was required in the previous method. The use of an accelerating ligand is essential to the success of reactions involving unreactive azides or alkynes. New mechanistic insights are provided, including the confirmation that a 1-iodoalkyne is formed as a key intermediate under the established conditions for the reaction.
Copper(i)-catalyzed cycloaddition of silver acetylides and azides: Incorporation of volatile acetylenes into the triazole core
Proietti Silvestri, Ilaria,Andemarian, Fikre,Khairallah, George N.,Wan Yap, Su,Quach, Tim,Tsegay, Sammi,Williams, Craig M.,O'Hair, Richard A. J.,Donnelly, Paul S.,Williams, Spencer J.
experimental part, p. 6082 - 6088 (2011/10/08)
Silver acetylides and organic azides react under copper(i) catalysis to afford 1,4-disubstituted 1,2,3-triazoles. Mechanistic studies implicate a process involving transmetallation to copper acetylides prior to cycloaddition. This work demonstrates that silver acetylides serve as suitable precursors for entry into copper-mediated coupling reactions. This methodology allows the incorporation of volatile and difficult-to-handle acetylenes into the triazole core.
