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

Molecules

Doohyun Lee³  Daehun Kim³  Seungyeon Lee³  Taegeum Kim³  Joobin Kim³  Sohee Kim³  Kwang-Hyeon Liu³  Sangkyu Lee³  Jong-Sup Bae³  Kyung-Sik Song³  Chang-Woo Cho²  Youn Kyung Son⁴  Dong Jae Baek⁵  Taeho Lee³  Wim Dehaen¹ 

[1] College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaDepartment of Chemistry, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, Korea;College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, Korea;National Institute of Biological Resources, Hwangyeong-ro 42, Seo-gu, Incheon 404-708, Korea;;College of Pharmacy, Natural Medicine Research Institute, Mokpo National University, 1666 Youngsan-ro, Muan-gun, Jeonnam 534-729, Korea

关键词: 1;    2;    3-triazoloamide;    solid-phase synthesis;    solution-phase synthesis;   

DOI  :  10.3390/molecules201119673

来源: mdpi

【 摘 要 】

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; S_N2 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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.