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

Masahito Murai, Koji Miki, Kouichi Ohe

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

(Chemical Equation Presented) Copper-catalyzed reactions of carbonyl-ene-nitriles with carbon nucleophiles, such as aromatics and ketones, afforded pyrrolin-2-ones (γ-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.

Original languageEnglish
Pages (from-to)9174-9176
Number of pages3
JournalJournal of Organic Chemistry
Volume73
Issue number22
DOIs
Publication statusPublished - Nov 21 2008
Externally publishedYes

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Nitriles
Addition reactions
Ketones
Copper
Lactams
Nucleophiles
Cyclization
Hydration
Carbon
ketimine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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. / Murai, Masahito; Miki, Koji; Ohe, Kouichi.

In: Journal of Organic Chemistry, Vol. 73, No. 22, 21.11.2008, p. 9174-9176.

Research output: Contribution to journalArticle

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