Organocatalytic enone-azide [3 + 2]-cycloaddition: synthesis of functionally rich C/N-double vinyl 1,2,3-triazoles

• Published in: Organic & biomolecular chemistry Vol. 18; no. 23; pp. 4470 - 4478
• Main Authors: Surendra Reddy, G, Suresh Kumar, A, Ramachary, Dhevalapally B
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 03.06.2020
• Subjects: Aromatic compounds; Crystal structure; Crystallography; Cycloaddition; NMR; Nuclear magnetic resonance; Reaction mechanisms; Room temperature; Selectivity; Substrates; Triazoles
• ISSN: 1477-0520; 1477-0539
• DOI: 10.1039/d0ob00848f

An enolate-mediated organocatalytic [3 + 2]-cycloaddition of enones with less reactive vinyl/alkyl/aryl azides is reported at room temperature for short reaction times. The metal-free amine-mediated catalytic conditions of this [3 + 2]-cycloaddition allowed us to synthesize a collection of C/N-double vinyl-1,2,3-triazoles and C-vinyl-1,2,3-triazoles through functionalized enones as quality azidophiles with various azides. It is an efficient catalytic [3 + 2]-cycloaddition for the synthesis of biologically important fully decorated C/N-double vinyl-1,2,3-triazoles with excellent outcomes with reference to the reaction rate, selectivity, operation simplicity, substrate scope, yields, and synthetic applications as demonstrated in the paper. Herein, we illustrated the importance of enolate reactivity with azides compared to enamines by correlation with previous enamine-mediated click reactions in the reaction mechanism section.