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

Ma, Guo-Yang
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Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Li, Ya-Fei
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Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Xu, Qing
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Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Ma, Yue-Yao
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Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Li, Ya-Wen
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Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Gong, Guo-Qiang
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Jilin Prov Prod Qual Supervis & Inspection Inst, Changchun 130012, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Zhang, Ning
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Jilin Prov Prod Qual Supervis & Inspection Inst, Changchun 130012, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Dang, Tan
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Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China

Wang, Kai-Kai
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Xinxiang Univ, Sch Pharm, Xinxiang 453003, Peoples R China Xinxiang Univ, Sch Chem & Mat Engn, Xinxiang 453003, Peoples R China
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
来源:
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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