Design and Synthesis of 1,2,3-Triazole-Fused Chiral Medium-Ring Benzo-Heterocycles, Scaffolds Mimicking Benzolactams
The Journal of Organic Chemistry2012Vol. 77(12), pp. 5399–5405
Citations Over TimeTop 10% of 2012 papers
Abstract
Based on "amide-triazole bioequivalence" principle, 1,2,3-triazole-fused chiral medium ring benzo-heterocycles capable of mimicking benzolactams were designed. Their syntheses were accomplished by cycloaddition of different sugar-derived azidoalkynes. While triazole-fused eight-membered benzo-heterocycles were formed by exclusive intramolecuclar [3 + 2] cycloaddition, attempted preparation of seven-membered analogues led to some intermolecular cycloaddition resulting in a dimeric macrocyclic product, in addition to intramolecular cycloaddition furnishing the expected heterocycle.
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