Citation: Hongwei Wang, Yongquan Ning, Paramasivam Sivaguru, Giuseppe Zanoni, Xihe Bi. [4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1, 2, 3-triazoles[J]. Chinese Chemical Letters, ;2022, 33(3): 1550-1554. doi: 10.1016/j.cclet.2021.09.008 shu

[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1, 2, 3-triazoles

Hongwei Wang ^{a, 1} ,
Yongquan Ning ^{a, 1} ,
Paramasivam Sivaguru ^a ,
Giuseppe Zanoni ^b ,
Xihe Bi ^{a, c, *,}

a.
Department of Chemistry, Northeast Normal University, Changchun 130024, China
b.
Department of Chemistry, University of Pavia, Viale Taramelli 12, Pavia 27100, Italy
c.
State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

bixh507@nenu.edu.cn

Received Date: 9 July 2021
Revised Date: 31 August 2021
Accepted Date: 1 September 2021
Available Online: 8 September 2021

Figures(5)

1-Substituted 1, 2, 3-triazoles represents 'privileged' structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1, 2, 3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.
- [4 + 1] Annulation,
- Azoalkene,
- Late-stage functionalization,
- 1-Substituted 1, 2, 3-triazoles
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