Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 24, Pages 12494-12504Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo402134x
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Funding
- 973 Program [2009CB939803]
- NSFC [21201164]
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CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.
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