Facile synthesis of spiro-heterocycles through one-pot multicomponent [3+3] cross 1,3-dipolar cycloaddition reactions

被引:0
作者
Ma, Guo-Yang [1 ]
Li, Ya-Fei [2 ]
Xu, Qing [2 ]
Ma, Yue-Yao [2 ]
Li, Ya-Wen [2 ]
Gong, Guo-Qiang [3 ]
Zhang, Ning [3 ]
Dang, Tan [1 ]
Wang, Kai-Kai [2 ]
机构
[1] Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China
[2] Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China
[3] Jilin Prov Prod Qual Supervis & Inspection Inst, Changchun 130012, Peoples R China
关键词
Spiro-heterocycles; Multicomponent; 3+3] cycloadditions; Nitrile imines; 4-Triazines; 1,2,4-Triazines; AZOMETHINE YLIDES; NITRILE IMINES; ACCESS;
D O I
10.1016/j.tet.2024.134328
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component 1,3-dipolar cycloaddition reaction involving ninhydrin, proline, and nitrile imines, which are generated in situ from hydrazonoyl chlorides, has been developed. This transformation can be conceptualized as a cross-1,3-dipolar cycloaddition reaction between two distinct ylides, proceeding via a [3 + 3] annulation pathway. This approach offers a swift route to a diverse array of novel and structurally intricate spiromultiheterocyclic skeletons, achieving good yields ranging from 80 % to 94 %. Furthermore, the chemical structure of a representative product has been rigorously confirmed via X-ray diffraction analysis.
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页数:6
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