Subscribe to RSS
DOI: 10.1055/s-0039-1691296
Conversion of N-Sulfonyl Triazoles into Triazole-Fused Isoindolines
Access to 1,2,3-Triazole-Fused Isoindolines via an Unexpected Lewis Acid Catalyzed Cyclization Reaction.
Tetrahedron Lett. 2019;
60
DOI: 10.1016/j.tetlet.2019.151151
Publication History
Publication Date:
18 November 2019 (online)
Significance
The initial aim of this study was to build on the previous development of the reaction of N-sulfonyl 1,2,3-triazoles with water under rhodium catalysis to form 2-aminoindanones (S. Xing et al. Org. Chem. Front. 2019, 6, 3121), but the use of anilines in place of water unexpectedly resulted in a completely different reaction pathway to form 1,2,3-triazole-fused isoindolines. Interestingly, under rhodium catalysis no product was observed, but under Lewis acid conditions isoindoline products were formed. The reaction is reasonably expected to proceed through transfer of the sulfonyl group to the aniline and subsequent intramolecular Michael reaction on the adjacent electron-deficient alkene.
#
Comment
Synthetic approaches to substituted 1,2,3-triazoles are limited, and this work provides a unique approach to polycyclic triazole-containing structural motifs. It would be interesting if this Lewis acid catalyzed, deprotection-triggered cyclization process could be applied to access other triazole-fused ring systems.
#
#