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Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-10 00:00:00 , DOI: 10.1021/acs.orglett.7b03719 Maria C. DiPoto 1 , Jimmy Wu 1
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-10 00:00:00 , DOI: 10.1021/acs.orglett.7b03719 Maria C. DiPoto 1 , Jimmy Wu 1
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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.
中文翻译:
(3 + 2)氮杂烯丙基阳离子的环状合成2-氨基咪唑酮和咪唑酮
报道了在氮杂氧基烯丙基阳离子与氰胺和腈之间环化(3 + 2)的第一个实例,以给出相应的2-氨基咪唑啉酮和咪唑啉酮。基于用某些底物分离出意料不到的亚氨酸酯产物的基础,提出了反应通过快速的动力学O-烷基化,然后重排为热力学上有利的2-氨基咪唑酮和咪唑酮来进行。该方法用于降压药厄贝沙坦的形式合成。
更新日期:2018-01-10
中文翻译:
(3 + 2)氮杂烯丙基阳离子的环状合成2-氨基咪唑酮和咪唑酮
报道了在氮杂氧基烯丙基阳离子与氰胺和腈之间环化(3 + 2)的第一个实例,以给出相应的2-氨基咪唑啉酮和咪唑啉酮。基于用某些底物分离出意料不到的亚氨酸酯产物的基础,提出了反应通过快速的动力学O-烷基化,然后重排为热力学上有利的2-氨基咪唑酮和咪唑酮来进行。该方法用于降压药厄贝沙坦的形式合成。