121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-490
Subject Lewis acid-Mediated [3+2+1] Annulation for the Construction of 2-Arylpyridines and Their Applications
Authors JiHyeon Ha, Yong Rok Lee*
Division of Chemical Engineering, Yeungnam University, Korea
Abstract

This abstract deals with the construction of diverse 2-phenylpyridines bearing benzophenone moieties by Lewis acid-mediated [3+2+1] annulation. This methodology provides a simple and convenient method for the synthesis of biologically important core molecules of nitrogen heterocycles. Importantly, 2-phenylpyridines are also used as building blocks in the synthesis of valuable ligands for metal complexes in organic transformations. Owing to their importance, several synthetic approaches have been reported based on transition-metal catalyzed or metal-free conditions. Although several approaches for the synthesis of 2-arylpyridines have been developed, a more facile and efficient one-pot synthetic protocol is still desirable. To date, there are no reports on [3+2+1] annulations for the synthesis of 2-arylpyridines using acetonitrile as a nitrogen source instead of ammonia, ammonium acetate and azide. As part of our interest in this area, we report herein a novel BF3∙OEt2 mediated [3+2+1] annulation of commercially available 3-formylchromones with aryl acetylenes, and acetonitrile for the construction of diverse 2-arylpyridines (Scheme 1). Interestingly, in this reaction, the nitrogen source for the 2-arylpyridine construction is from the solvent, acetonitrile, rather than ammonium acetate or the amine. This new developed protocol lets an application for the one-pot synthesis of N-heterocycles as potent UV filters and antibacterial agents.

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