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通过铜催化的一锅法点击反应和分子内芳基化反应设计与合成1,2-二氢喹啉/色烯稠合糖三唑骨架

Design and synthesis of 1,2-dihydroquinoline/chromene fused sugar triazole frameworks by copper-catalyzed one-pot click and intramolecular arylation reactions.

作者信息

Ahemad Mohammed Ansar, Nayak Sabita, Prusty Kamalika, Panigrahi Gopinatha, Mohapatra Suhasini, Mohapatra Seetaram

机构信息

Organic Synthesis Laboratory, Department of Chemistry, Ravenshaw University, Cuttack-753003, Odisha, India.

出版信息

Org Biomol Chem. 2024 Aug 22;22(33):6748-6762. doi: 10.1039/d4ob00711e.

Abstract

Expedient copper-catalyzed one-pot click and intramolecular arylation reactions have been developed for the synthesis of 1,2-dihydroquinoline/chromene-fused triazoles with varying sugar functionalities. It has been observed that the additive TMEDA greatly facilitates this copper-catalyzed cyclization. This reaction involves two mechanistically distinct reactions an atom-economical click reaction and a direct arylation of a sugar triazole. This method provides rapid and simple access to fused sugar triazoles in moderate to good yields. All the key products were characterized using H and C NMR and HRMS data.

摘要

已开发出便捷的铜催化一锅法点击反应和分子内芳基化反应,用于合成具有不同糖官能团的1,2 - 二氢喹啉/色烯稠合三唑。据观察,添加剂N,N,N',N'-四甲基乙二胺(TMEDA)极大地促进了这种铜催化的环化反应。该反应涉及两个机理不同的反应——原子经济的点击反应和糖基三唑的直接芳基化反应。此方法能以中等至良好的产率快速简便地获得稠合糖基三唑。所有关键产物均通过氢核磁共振(H NMR)、碳核磁共振(C NMR)和高分辨质谱(HRMS)数据进行了表征。

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