Issue 4, 2022

Acid-catalyzed ring-expansion of 4-(1-hydroxycyclobutyl)-1,2,3-triazoles

Abstract

We here report a direct ring-opening/semipinacol rearrangement reaction of 4-(1-hydroxycyclobutyl)-1,2,3-triazole, in which N-acyl substituted 1,2,3-triazole was generated in situ and would trigger thermodynamically controlled electrocyclization ring-opening to afford a rearrangement precursor (α-diazo-ol). This strategy avoided the usage of metal catalysts and the reservation of sulfonyl groups on the N1-position of 1,2,3-triazole. The final cycloenaminone product is highly reactive and could be commonly used as a dinucleophilic acceptor to synthesize structurally diverse fused bicyclic products.

Graphical abstract: Acid-catalyzed ring-expansion of 4-(1-hydroxycyclobutyl)-1,2,3-triazoles

Supplementary files

Article information

Article type
Research Article
Submitted
22 Nov 2021
Accepted
03 Jan 2022
First published
06 Jan 2022

Org. Chem. Front., 2022,9, 1065-1069

Acid-catalyzed ring-expansion of 4-(1-hydroxycyclobutyl)-1,2,3-triazoles

M. Xu, L. Liu, T. Wang, H. Luo, M. Hou, L. Du, X. Xin, Q. Lu and B. Li, Org. Chem. Front., 2022, 9, 1065 DOI: 10.1039/D1QO01747K

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