I2/Aqueous TBHP-Catalyzed Coupling of Amides with Methylarenes/Aldehydes/Alcohols: Metal-Free Synthesis of Imides

被引：46

作者：

Aruri, Hariprasad ^{[1
,2
]}

Singh, Umed ^{[1
,2
]}

Kumar, Sanjay ^{[1
,2
]}

Kushwaha, Manoj ^{[3
]}

Gupta, Ajai Prakash ^{[3
]}

Vishwakarma, Ram A. ^{[1
,2
]}

Singh, Parvinder Pal ^{[1
,2
]}

机构：

[1] Indian Inst Integrat Med, CSIR, Med Chem Div, Canal Rd, Jammu 180001, India

[2] Indian Inst Integrat Med, CSIR, Qual Control & Qual Assurance, Canal Rd, Jammu 180001, India

[3] Acad Sci & Innovat Res, Canal Rd, Jammu 180001, India

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 15期

关键词：

ISOGRANULATIMIDE ANALOGS; N-ACYLATION; ALDEHYDES; AMINES; AMIDATION; THALIDOMIDE; MECHANISMS; ANIRACETAM;

D O I：

10.1021/acs.orglett.6b01684

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We present a metal-free method for the synthesis of imides by the direct coupling of NH-amides with methylarenes under iodine/aqueous TBHP conditions. The optimized conditions worked very well with benzaldehydes and benzyl alcohol and furnished the corresponding imides in good to excellent yields. A series of control and radical scavenger experiments were also performed, which suggested the involvement of radical pathways. The labeling experiment in the presence of O-18-labeled H2O suggested water as a source of oxygen in the imides.

引用

页码：3638 / 3641

页数：4

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