One-Pot Synthesis of 3-Iminoisoindolinones by a Rhodium(III)-Catalyzed and Methanol-Assisted C-H Cyanation-Cyclization Cascade with N-Alkoxyl Transfer

被引：12
|
作者：
Jia, Jinlong [1 ]
Liu, Xuelei [1 ]
Shi, Jingjing [1 ]
Xu, H. Eric [1 ,2 ]
Yi, Wei [1 ]
机构：
[1] Chinese Acad Sci, Shanghai Inst Mat Medica, Ctr Struct & Funct Drug Targets, VARI SIMM Ctr,Key Lab Receptor Res, Shanghai 201203, Peoples R China
[2] Van Andel Res Inst, Lab Struct Sci, Program Struct Biol & Drug Discovery, Grand Rapids, MI 49503 USA
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 4卷 / 11期
关键词：
C-H functionalization; 3-iminoisoindolinones; N-alkoxybenzamides; N-cyano-N-phenyl-p-toluenesulfonamide; rhodium; PHENYL-P-TOLUENESULFONAMIDE; BOND FUNCTIONALIZATIONS; ISOINDOLINE DYES; ACTIVATION; ARENES; OXIDES; HETEROCYCLES; INDOLES; ALKYNES;
D O I：
10.1002/ajoc.201500294
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we disclose the Rh-III-catalyzed and MeOH-assisted direct C-H functionalization of simple N-alkoxybenzamides with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) in a one-pot cascade synthesis of 3-iminoisoindolinones with excellent substrate/functional group tolerance. Experimental studies reveal that the versatile reaction comprises a regioselective C-H cyanation and subsequent intramolecular cyclization along with N-alkoxyl transfer. Furthermore, the synthetic application of the obtained products to rapidly build other important structural motifs, such as lactams and phthalazinones, has also been demonstrated in subsequent derivatization reactions.
引用
收藏
页码：1250 / 1253
页数：4
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