A novel and convenient route for the construction of 5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indoles and its application in the synthesis of Rizatriptan |
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Authors: | Yi He Xiaolong Li Jue Li Xiaocen LiLi Guo Li Hai Yong Wu |
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Affiliation: | Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, PR China |
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Abstract: | In this study, a novel and convenient route for the construction of 5-((1H-1,2,4-triazol-1-yl)methyl)-1H-indoles (8) is presented starting from (1H-1,2,4-triazol-1-yl)methanol (5) and indolines (6) under 98% H2SO4 at room temperature for 4–24 h, followed by deacetylation and dehydrogenation. Based on this finding, a novel route to synthesize Rizatriptan starting from tryptamine was designed and accomplished with 48.5% overall yield in 6 steps. Compared with operational art, the new route afforded higher yield and more pure products requiring no chromatographic purification, which may further be applied in industrialization. |
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Keywords: | (1H-1,2,4-Triazol-1-yl)methanol Tryptamine 5-((1H-1,2,4-Triazol-1-yl)methyl)-1H-indoles Rizatriptan |
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