氮丙啶鎓阳离子的[3+2]环加成反应合成 2-氨基咪唑啉酮和咪唑啉酮
Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations.
机构信息
Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.
出版信息
Org Lett. 2018 Feb 2;20(3):499-501. doi: 10.1021/acs.orglett.7b03719. Epub 2018 Jan 10.
Abstract
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.
摘要
首次报道了氮丙啶鎓阳离子与氰酰胺和腈的（3 + 2）环加成反应，得到相应的 2-氨基咪唑啉酮和咪唑啉酮。基于某些底物中分离出意想不到的异氰酸酯产物，提出反应通过快速动力学 O-烷基化进行，然后重排得到热力学上有利的 2-氨基咪唑啉酮和咪唑啉酮。该方法被应用于抗高血压药物厄贝沙坦的形式合成。
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