Convenient generation of 1,3-dipolar nitrilimines and [3+2] cycloaddition for the synthesis of spiro compounds

被引：2
作者：
Zhu, Mei-Jun [1 ]
Ye, Rong [2 ]
Shi, Wen-Jing [2 ]
Sun, Jing [2 ]
Yan, Chao-Guo [2 ]
机构：
[1] Jianghai Polytechn Coll, Yangzhou 225000, Peoples R China
[2] Yangzhou Univ, Coll Chem & Chem Engn, Yangzhou 225002, Peoples R China
来源：
TETRAHEDRON LETTERS | 2022年 / 110卷
基金：
中国国家自然科学基金;
关键词：
Nitrilimine 1,3-dipolar cycloaddition; Aldohydrazone; Tetraazaspiro[4.5]dec-1-ene; Spiro[indene-2,40-pyrazole; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; MOLECULAR DIVERSITY; AZOMETHINE YLIDES; NITRILE IMINES; TEMPO; CONSTRUCTION; DERIVATIVES; ACCESS; CYTOTOXICITY;
D O I：
10.1016/j.tetlet.2022.154186
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In the presence of 2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) as an oxidizer, the domino [3 + 2] cycloaddition reaction of aldohydrazones with 2-arylidene-1,3-indnaediones or 5-arylidene-1,3-dimethylbarbituric acids in acetonitrile at 80 degrees C afforded functionalized spiro[indene-2,4'-pyrazoles]1,3-diones or 2,3,7,9-tetraazaspiro[4.5]dec-1-ene-6,8,10-triones in satisfactory yields. This reaction was believed to proceed with in situ generation of reactive 1,3-dipolar nitrilimine and its sequential 1,3-dipolar cycloaddition reaction with cyclic dipolarophiles. Thus, a new convenient synthetic method for the active dipolar nitrilimine was successfully developed. (C) 2022 Elsevier Ltd. All rights reserved.
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页数：4
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