Synthesis of 4-Imidazolidinones from Diamides and Ethynyl Benziodoxolones via Double Michael-Type Addition: Ethynyl Benziodoxolones as Electrophilic Ynol Synthons

被引：7

作者：

Shimizu, Ayaka ^{[2
]}

Shibata, Atsushi ^{[2
]}

Kano, Takashi ^{[2
]}

Kumai, Yuuichi ^{[2
]}

Kawakami, Ryouhei ^{[2
]}

Esaki, Hiroyoshi ^{[1
,2
]}

Fukushima, Kazuaki ^{[1
]}

Tada, Norihiro ^{[1
,2
]}

Itoh, Akichika ^{[1
,2
]}

机构：

[1] Hyogo Med Univ, Nishinomiya, Hyogo 6638501, Japan

[2] Gifu Pharmaceut Univ, Gifu 5011196, Japan

来源：

ORGANIC LETTERS | 2022年 / 24卷 / 48期

关键词：

ALKYNYLATION; VINYL; CONDENSATION; ENAMIDES; ARYL;

D O I：

10.1021/acs.orglett.2c03648

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The moiety of 4-imidazolidinone is an important structural motif in organic synthesis and medicinal chemistry. We present the synthesis of 4-imidazolidinones from various diamides with ethynyl benziodoxolones through double Michael-type addition, which is an unprecedented reaction mode for hypervalent alkynyl iodine compounds. cis-2,5-Disubstituted 4-imidazolidinones were diastereoselectively synthesized from amino acid derived diamides. Having derivatized the 4-imidazolidinones, several control experiments and density functional theory calculations were conducted to realize mechanistic insight.

引用

页码：8859 / 8863

页数：5