通过5-氨基-1,2,3-三唑的脱氮转化合成官能化1-咪唑
Synthesis of Functionalized 1-Imidazoles via Denitrogenative Transformation of 5-Amino-1,2,3-Triazoles.
作者信息
Gribanov Pavel S, Philippova Anna N, Smol'yakov Alexander F, Tukhvatullina Diana N, Vlasova Viktoria A, Topchiy Maxim A, Asachenko Andrey F, Osipov Sergey N
机构信息
A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28/1 Vavilova Str., 119334 Moscow, Russia.
D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047 Moscow, Russia.
出版信息
Molecules. 2025 Mar 21;30(7):1401. doi: 10.3390/molecules30071401.
An efficient access to novel 2-substituted 1-imidazole derivatives was developed based on acid-mediated denitrogenative transformation of 5-amino-1,2,3-triazole derivatives available through dipolar azide-nitrile cycloaddition (DCR). The proposed approach includes intramolecular cyclization of 5-amino-4-aryl-1-(2,2-diethoxyethyl) 1,2,3-triazoles followed by triazole ring opening and insertion of in situ formed carbene intermediate into the O-H bond of different alcohols under acidic conditions.
基于通过偶极叠氮化物-腈环加成反应（DCR）可得的5-氨基-1,2,3-三唑衍生物的酸介导脱氮转化，开发了一种有效合成新型2-取代-1-咪唑衍生物的方法。所提出的方法包括5-氨基-4-芳基-1-(2,2-二乙氧基乙基)1,2,3-三唑的分子内环化，随后三唑环开环，并在酸性条件下将原位形成的卡宾中间体插入不同醇的O-H键中。
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