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.
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.
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DOI：
10.1021/jo801776v
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发表时间：
2008-11
期刊：
影响因子：
--
通讯作者：
Masahito Murai;K. Miki;K. Ohe
中科院分区：
文献类型：
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作者：
Masahito Murai;K. Miki;K. Ohe
在铜催化下，羰基-烯-腈与含碳亲核试剂（如芳烃和酮）反应，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-环己烯酮中间体的酮亚胺部分的加成反应，其通过腈部分的水合随后脱水环化形成。
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.