Water-Mediated Selective Synthesis of Pyrazolo[1,5-a]quinazolin-5(4H)-ones and [1,2,4]Triazolo[1,5-a]quinazolin-5(4H)-one via Copper-Catalyzed Cascade Reactions |
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| Authors: | Xinying Zhang Lin Gao Zhangxin Wang Xuesen Fan |
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| Institution: | 1. School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Green Chemical Media and Reactions, Henan Normal University, Xinxiang, Henan, Chinaxinyingzhang@htu.cn xuesen.fan@htu.cn;3. School of Chemistry and Chemical Engineering, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Key Laboratory of Green Chemical Media and Reactions, Henan Normal University, Xinxiang, Henan, China |
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| Abstract: | A convenient and sustainable synthesis of pyrazolo1,5-a]quinazolin-5(4H)-ones and 1,2,4]triazolo1,5-a]quinazolin-5(4H)-one through copper-catalyzed cascade reactions of 2-bromobenzoates with 1H-pyrazol-5-amines or 1H-1,2,4-triazol-5-amine under ligand-free conditions in water is presented. It is notable that aqueous medium turned out to be crucial for the chemoselective formation of the title compounds. Compared with literature protocols, this new method showed advantages such as simple and sustainable procedure, commercially available starting materials, and convenient reuse of the reaction medium together with the copper catalyst. |
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| Keywords: | Cascade reaction copper catalysis pyrazolo[1 5-a]quinazolinone [1 2 4]triazolo[1 5-a]quinazolinone |
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