119th General Meeting of the KCS

Type Poster Presentation
Area 의약화학
Room No. 포스터발표장
Time 4월 20일 (목요일) 11:00~12:30
Code MEDI.P-418
Subject SYNTHESIS OF 1,2,3-TRIAZOLES VIA CYCLOADDITION OF β-KETOPHOSPHONATE WITH AZIDE
Authors 이두현, 김다현, 이태호*
경북대학교 약학과, Korea
Abstract 1,2,3-Triazoles, which are non-classic bioisosteres of amides, are important heterocycles in medicinal chemistry and material science. Because of their widespread applications, a number of copper(I)-catalyzed azide-alkyne cycloaddition reactions for the preparation of 1,4-substituted 1,2,3-triazoles have been performed. However, synthetic methods for the preparation of 1,5-substituted 1,2,3-triazoles have been known as restricted. Also, these known methods have usually used limited terminal alkyne and expensive ruthenium-catalysts. Therefore, the development of new efficient methods for the preparation of 1,5-substituted 1,2,3-triazoles is still demanded. β-Ketophosphonates are well-known and important intermediate in organic synthesis. They are widely used for the synthesis of α,β -unsaturated carbonyl compounds via Horner-Wadsworth-Emmons (HWE) olefination and for the synthesis of β-amino phosphonate compounds via Mannich-type reaction, and for the synthesis of phosphonylated heterocyclic compounds. Herein, we report the general and efficient cycloaddition reaction of β-ketophosphonate with azide for the preparation of 1,5-disubstituted 1,2,3-triazoles and 1,5-disubstituted 4-phosphoryl 1,2,3-triazoles under basic conditions.
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