Synthesis of Spiro-lactams and Polysubstituted Pyrroles via Ceric Ammonium Nitrate-Mediated Oxidative Cyclization of N-Furan-2-ylmethyl-β-Enaminones

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• 作者：Hui Peng ; Jiuyi Li ; Furong Wang ; Bo Liu ; Biaolin Yin
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：June 17, 2016
• 年：2016
• 卷：81
• 期：12
• 页码：4939-4946
• 全文大小：377K
• 年卷期：0
• ISSN：1520-6904

文摘

Spiro-lactams and polysubstituted pyrroles were synthesized by reactions of furfurylamines with ynones followed by oxidation. Specifically, the protocol involved in situ generation of N-furan-2-ylmethyl-β-enaminones and their subsequent oxidation by ceric ammonium nitrate (6 equiv for spiro-lactam formation, 3 equiv for pyrrole formation). This useful dearomatizing oxidation, which likely proceeds via a free-radical pathway, can be expected to extend the synthetic applications of furan and pyrrole derivatives.