CuI-Catalyzed Aerobic Oxidative 伪-Aminaton Cyclization of Ketones to Access Aryl or Alkenyl-Substituted Imidazoheterocycles

详细信息    查看全文

• 作者：Yuanfei Zhang ; Zhengkai Chen ; Wenliang Wu ; Yuhong Zhang ; Weiping Su
• 刊名：Journal of Organic Chemistry
• 出版年：2013
• 出版时间：December 20, 2013
• 年：2013
• 卷：78
• 期：24
• 页码：12494-12504
• 全文大小：515K
• 年卷期：v.78,no.24(December 20, 2013)
• ISSN：1520-6904

文摘

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鈥揔ing reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.