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.

引用

页数：4

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