Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines

详细信息    查看全文

• 作者：Xue-Qiang Chu ; Wen-Bin Cao ; Xiao-Ping Xu ; Shun-Jun Ji
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：82
• 期：2
• 页码：1145-1154
• 全文大小：701K
• ISSN：1520-6904

文摘

An efficient method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C–H bond functionalization. Control experiments were performed to gain deep understanding of the mechanism, and the reactions are likely to proceed through a designed TEMPO complexation/enamine addition/transient α-occupation/β-TEMPO elimination/cyclization sequence.