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- Title
Alkyl Propiolates Participated [3+2] Annulation for the Switchable Synthesis of 1,5‐ and 1,4‐Disubstituted 1,2,3‐Triazoles Containing Ester Side Chain.
- Authors
Cao, Shuo; Liu, Yunyun; Wan, Jie‐Ping; Hu, Changfeng; Wen, Chengping
- Abstract
By means of a featured enamine activation, the alkyl propiolates have been successfully employed in the [3+2] annulation for the synthesis of 1,2,3‐triazoles. The synthesis of both 1,4‐ as well as the hardly available 1,5‐disubstituted 1,2,3‐triazoles can be selectively accessed by using tosyl azide and tosyl hydrazine as nitrogen source, respectively. Enamine activation for annulation: The enamine activation on alkyl propiolates enables the switchable synthesis of 1,5‐ and 1,4‐disubstituted 1,2,3‐triazoles bearing ester side chain. The selective synthesis of 1,2,3‐triazoles with different substitution styles are realized by employing different hydrogen atom sources of tosyl hydrazine and tosyl azide. The annulation of both 1,2,3‐triazole rings takes place under transition metal‐free condition, providing sustainable new routes in the synthesis of structurally divergent 1,2,3‐triazole scaffolds.
- Subjects
TRIAZOLES synthesis; ANNULATION; ENAMINES; AZIDES; HYDRAZINE; REGIOSELECTIVITY (Chemistry)
- Publication
ChemCatChem, 2018, Vol 10, Issue 21, p5021
- ISSN
1867-3880
- Publication type
Article
- DOI
10.1002/cctc.201801366