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Molecules 2015, 20(11), 19984-20013; doi:10.3390/molecules201119673

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

1
College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, Korea
2
Department of Chemistry, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, Korea
3
National Institute of Biological Resources, Hwangyeong-ro 42, Seo-gu, Incheon 404-708, Korea
4
College of Pharmacy, Natural Medicine Research Institute, Mokpo National University, 1666 Youngsan-ro, Muan-gun, Jeonnam 534-729, Korea
*
Authors to whom correspondence should be addressed.
Academic Editors: Wim Dehaen and Derek J. McPhee
Received: 16 September 2015 / Revised: 28 October 2015 / Accepted: 29 October 2015 / Published: 5 November 2015
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [3027 KB, uploaded 5 November 2015]   |  

Abstract

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. View Full-Text
Keywords: 1,2,3-triazoloamide; solid-phase synthesis; solution-phase synthesis 1,2,3-triazoloamide; solid-phase synthesis; solution-phase synthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Lee, D.; Kim, D.; Lee, S.; Kim, T.; Kim, J.; Kim, S.; Liu, K.-H.; Lee, S.; Bae, J.-S.; Song, K.-S.; Cho, C.-W.; Son, Y.K.; Baek, D.J.; Lee, T. Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches. Molecules 2015, 20, 19984-20013.

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