Silver-catalyzed nitration/annulation of 2-alkynylanilines for a tunable synthesis of nitrated indoles and indazole-2-oxides

被引：23
|
作者：
Zhang, Tian-Shu [1 ]
Wang, Rong [2 ]
Cai, Pei-Jun [1 ]
Hao, Wen-Juan [2 ]
Tu, Shu-Jiang [2 ]
Jiang, Bo [2 ]
机构：
[1] China Univ Min & Technol, Sch Chem Engn & Lichnoloo, Xuzhou 221116, Jiangsu, Peoples R China
[2] Jiangsu Normal Univ, Sch Chem & Mat Sci, Jiangsu Key Lab Green Synthet Chem Funct Mat, Xuzhou 221116, Jiangsu, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2019年 / 6卷 / 16期
关键词：
FREE NITRO-CARBOCYCLIZATION; HIGHLY EFFICIENT SYNTHESIS; TERT-BUTYL NITRITE; AROMATIC-COMPOUNDS; T-BUONO; C-N; CYCLIZATION; ALKENES; (BUONO)-BU-T; 1,7-ENYNES;
D O I：
10.1039/c9qo00715f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two new types of silver-catalyzed nitration-annulations of 2-alkynylanilines with tert-butyl nitrite (TBN) were reported, leading to the selective formation of a variety of nitrated indoles and indazole-2-oxides by changing the N-protection of 2-alkynylanilines. Ag-Catalyzed nitration-annulation of N-sulfonyl 2-alkynylanilines without C4 substituents afforded 5-nitroindoles under neutral-redox conditions, whereas the presence of C5 substituents gave 7-nitroindoles through silver catalysis. N-Methyl 2-alkynylanilines underwent a completely different process to furnish aroyl indazole-2-oxides.
引用
收藏
页码：2968 / 2973
页数：6
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