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JOURNAL ARTICLE
RESEARCH SUPPORT, N.I.H., EXTRAMURAL
Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations.
Organic Letters 2018 Februrary 3
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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