Structure and Additive-free Transamidation of Planar N-Cyano Amides

被引：7

作者：

Yamasaki, Ryu ^{[1
]}

Okada, Yuko ^{[1
]}

Iizumi, Hiromi ^{[1
]}

Ito, Ai ^{[1
]}

Fukuda, Kazuo ^{[1
]}

Okamoto, Iwao ^{[1
]}

机构：

[1] Showa Pharmaceut Univ, Tokyo 1948543, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 09期

关键词：

CATALYZED TRANSAMIDATION; CYANAMIDE ALKENES; QUINAZOLINONES; CYCLIZATION; CLEAVAGE; ACCESS;

D O I：

10.1021/acs.joc.3c00172

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Although transamidation of amides generally requires metals, additives, or harsh conditions, we present here a facile transamidation of Ncyano amides with various amines at ambient temperature without any additive. N-cyano amides preferred the trans conformation and have a reduced double bond character revealed by crystal analysis. The DFT study indicates that the transamidation reaction proceeds through the direct attack of amine on the amide carbonyl since the LUMO (or LUMO+1) is located at the carbonyl moiety.

引用

页码：5704 / 5712

页数：9

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