Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches
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 constru...
| Main Authors: | , , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2015-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/11/19673 |
| _version_ | 1819228542933663744 |
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| author | 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 |
| author_facet | 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 |
| author_sort | Doohyun Lee |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-23T10:58:57Z |
| format | Article |
| id | doaj.art-9a8aad86992b4480b6dabd9530e3dfc0 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T10:58:57Z |
| publishDate | 2015-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-9a8aad86992b4480b6dabd9530e3dfc02022-12-21T17:49:41ZengMDPI AGMolecules1420-30492015-11-012011199842001310.3390/molecules201119673molecules201119673Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic ApproachesDoohyun Lee0Daehun Kim1Seungyeon Lee2Taegeum Kim3Joobin Kim4Sohee Kim5Kwang-Hyeon Liu6Sangkyu Lee7Jong-Sup Bae8Kyung-Sik Song9Chang-Woo Cho10Youn Kyung Son11Dong Jae Baek12Taeho Lee13College of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaCollege 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, KoreaNational Institute of Biological Resources, Hwangyeong-ro 42, Seo-gu, Incheon 404-708, KoreaCollege of Pharmacy, Natural Medicine Research Institute, Mokpo National University, 1666 Youngsan-ro, Muan-gun, Jeonnam 534-729, KoreaCollege of Pharmacy, Research Institute of Pharmaceutical Sciences, Kyungpook National University, 80 Daehak-ro, Buk-gu, Daegu 702-701, KoreaEfficient 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.http://www.mdpi.com/1420-3049/20/11/196731,2,3-triazoloamidesolid-phase synthesissolution-phase synthesis |
| spellingShingle | 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 Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches Molecules 1,2,3-triazoloamide solid-phase synthesis solution-phase synthesis |
| title | Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches |
| title_full | Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches |
| title_fullStr | Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches |
| title_full_unstemmed | Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches |
| title_short | Efficient Syntheses of 1,2,3-Triazoloamide Derivatives Using Solid- and Solution-Phase Synthetic Approaches |
| title_sort | efficient syntheses of 1 2 3 triazoloamide derivatives using solid and solution phase synthetic approaches |
| topic | 1,2,3-triazoloamide solid-phase synthesis solution-phase synthesis |
| url | http://www.mdpi.com/1420-3049/20/11/19673 |
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