铜催化芳烃和酮与2-氮杂-2,4-环戊二烯酮的加成反应：羰基-烯-腈向1H-吡咯啉-2(5H)-酮的简便高效转化。
Copper-catalyzed addition reactions of aromatics and ketones to 2-aza-2,4-cyclopentadienone: facile and efficient transformation of carbonyl-ene-nitriles to 1H-pyrrolin-2(5H)-ones.
作者信息
Murai Masahito, Miki Koji, Ohe Kouichi
机构信息
Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
出版信息
J Org Chem. 2008 Nov 21;73(22):9174-6. doi: 10.1021/jo801776v. Epub 2008 Oct 17.
PMID:18925786
Abstract
Copper-catalyzed reactions of carbonyl-ene-nitriles with carbon nucleophiles, such as aromatics and ketones, afforded pyrrolin-2-ones (gamma-lactam) in excellent yield. The reaction mechanism involves addition reactions with a ketimine moiety of the 2-aza-2,4-cyclopentadienone intermediate, which is formed via hydration of a nitrile moiety followed by dehydrative cyclization.
摘要
铜催化羰基烯腈与碳亲核试剂（如芳烃和酮）的反应，能以优异的产率得到吡咯啉-2-酮（γ-内酰胺）。反应机理涉及与2-氮杂-2,4-环戊二烯酮中间体的酮亚胺部分的加成反应，该中间体是通过腈部分的水合作用，然后脱水环化形成的。
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