1-甲酰基-1,2,3-三唑的串联合成
Tandem synthesis of 1-formyl-1,2,3-triazoles.
作者信息
Fletcher James T, Christensen Joseph A, Villa Eric M
机构信息
Department of Chemistry, Creighton University, 2500 California Plaza, Omaha, NE 68178, U.S.A.
出版信息
Tetrahedron Lett. 2017 Nov 22;58(47):4450-4454. doi: 10.1016/j.tetlet.2017.10.023. Epub 2017 Oct 13.
Abstract
A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.
摘要
开发了一种通过两步一锅法缩醛裂解/CuAAC反应制备4-甲酰基-1,2,3-三唑的串联方法。使用该方法，以良好的收率和纯度制备了具有吸电子和供电子取代基的4-甲酰基-1,2,3-三唑类似物。该方法扩展到包含叠氮化物取代额外步骤的三步串联反应也取得了成功，避免了有机叠氮化物的分离。这种一锅法以其简单性和温和条件而值得注意，它使用实用、易于获得的反应物，并依靠质子溶剂促进酸催化的缩醛裂解。
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