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2005
Imidazole derivatives
R 0190
N—H Insertion Reactions of Primary Ureas: The Synthesis of Highly Substituted
and Imidazoles from Diazocarbonyls. — Rh-catalyzed treatment of
20- 119 Imidazolones
various diazocarbonyls with primary ureas results in regioselective formation of N-H
insertions products of type (III). In the presence of acid, the latter undergo ring closure
to afford imidazolones which can smoothly be converted into 1,3-disubstituted imidazolones and 2-substituted imidazoles. Interestingly, the ketoamide analogue (XII)
does not undergo N-H insertion but C-H insertion reaction yielding the indole (XIII).
— (LEE, S.-H.; YOSHIDA, K.; MATSUSHITA, H.; CLAPHAM, B.; KOCH, G.;
ZIMMERMANN, J.; JANDA*, K. D.; J. Org. Chem. 69 (2004) 25, 8829-8835; Dep.
Chem., Scripps Res. Inst., San Diego, La Jolla, CA 92037, USA; Eng.) — Jannicke
2005
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