Cs2CO3 Catalyzed Intramolecular Aminocarbonylation of Alkynes: Synthesis of 3-Amino-1H-inden-1-ones from N-tert-Butyl-2-(1-alkynyl)benzaldimines

被引：5
|
作者：
Guo, Zhen [1 ]
Liu, Tao [1 ]
Liang, Xiujuan [1 ]
Wu, Yuting [1 ]
Yao, Tuanli [1 ]
机构：
[1] Shaanxi Univ Sci & Technol, Coll Chem & Chem Engn, Shaanxi Key Lab Chem Additives Ind, Xian 710021, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 05期
关键词：
aminocarbonylation; 3-amino-indenone; N-tert-butyl-2-(1-alkynyl)benzaldimines; catalysis; cesium carbonate; CYCLIZATION; RULES; DERIVATIVES; LIGANDS;
D O I：
10.1002/adsc.201901349
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Synthesis of a wide variety of 3-amino-1H-inden-1-ones from N-tert-butyl-2-(1-alkynyl)benzaldimines via intramolecular aminocarbonylation of alkynes using Cs2CO3 as catalyst and air as oxidant has been developed. This highly atom-efficient, transition-metal-free reaction proceeds under thermal conditions. We propose that the reaction proceeds through an unprecedented 5-exo-dig cyclization of N-tert-butyl-2-(1-alkynyl)benzaldimines and thermal rearrangement of 3-methylene-2 lambda(2)-isoindolin-1-ols.
引用
收藏
页码：1053 / 1057
页数：5
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