Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches

• Main Authors: Doohyun Lee, Daehun Kim, Seungyeon Lee, Taegeum Kim, Joobin Kim, Sohee Kim, Kwang-Hyeon Liu, Sangkyu Lee, Jong-Sup Bae, Kyung-Sik Song, Chang-Woo Cho, Youn Kyung Son, Dong Jae Baek, Taeho Lee
• Format: Article
• Language: English
• Published: MDPI AG 2015-11-01
• Series: Molecules
• Subjects: 1,2,3-triazoloamide; solid-phase synthesis; solution-phase synthesis
• Online Access: http://www.mdpi.com/1420-3049/20/11/19673

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.