Synthesis of 2-Aminoimidazolones and Imidazolones by (3+2) Annulation of Azaoxyallyl Cations

被引：73

作者：

DiPoto, Maria C. ^{[1
]}

Wu, Jimmy ^{[1
]}

机构：

[1] Dartmouth Coll, Dept Chem, Hanover, NH 03755 USA

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 03期

关键词：

AZA-OXYALLYL CATIONS; CYCLOADDITION REACTIONS; ACCESS; DERIVATIVES;

D O I：

10.1021/acs.orglett.7b03719

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first examples of (3 +, 2) annulations between azaoxyallyl cations and cyanamides and nitriles, to give, the corresponding 2-aminoimidazolones and imidazolones, are reported. On the basis of the isolation of unexpected imidate products with certain substrates, it is proposed that the reaction proceeds via fast kinetic O-alkylation followed by rearrangement to the thermodynamically favored 2-aminoimidazolones and imidazolones. The method was applied to the formal synthesis of the antihypertensive drug irbesartan.

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页码：499 / 501

页数：3

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