Efficient methodologies for the synthesis of 1,2,3-triazoles and 4',6'-diaryl-2'-hydroxyacetophenones

• Main Authors: Kuo, Chia-Ming, 郭家銘
• Other Authors: Yao, Ching-Fa
• Format: Others
• Language: zh-TW
• Published: 2013
• Online Access: http://ndltd.ncl.edu.tw/handle/42105465926059837927

碩士 === 國立臺灣師範大學 === 化學系 === 101 === This thesis covers the combination of two separate work accomplished during the throughout the study. Among them, the first work deals with a solvent free copper (II) catalyzed azide alkynes cycloaddition reaction. In this project, we achieved a new procedure for azide alkyne cycloaddition reaction in the presence copper acetate and CTAB. Using this procedure, a variety of non chelating azide converted into different structurally diverse triazole derivatives by the reaction with various alkynes. This procedure is equally efficient for the synthesis of bis and tris trialzoles as well. Number functional groups were well tolerated under the described reaction conditions. Easy handling, the use of copper(II) catalyst in absence of reducing agents, rapid and clean reactions, and easy isolation of the products are important features of this method. Second part of the thesis describes a one pot synthesis 2-hydroxy acetophenones from the reaction of 1,3-disubstitutedprop-2-yn-1-one and 1,3-diketones in presence of DBU. This reaction involves Michael addition of 1,3-diketones followed by aldol condensation. This method was applied for the synthesis of different diarylasubstituted hydroxyacetophones in good to moderate yields. Further, similar reaction ketoester and 2-Acetylbutyrolactone provided different compounds. Mechanistic routes for the formation of all the products were rationalized through experimental evidence. Keywords:triazoles、acetophenones