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 language | English |
|---|---|
| Pages (from-to) | 9174-9176 |
| Number of pages | 3 |
| Journal | Journal of Organic Chemistry |
| Volume | 73 |
| Issue number | 22 |
| DOIs | |
| Publication status | Published - Nov 21 2008 |
| Externally published | Yes |
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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 journal › Article
}
TY - JOUR
T1 - Copper-catalyzed addition reactions of aromatics and ketones to 2-aza-2,4-cyclopentadienone
T2 - Facile and efficient transformation of carbonyl-ene-nitriles to 1H-pyrrolin-2(5H)-ones
AU - Murai, Masahito
AU - Miki, Koji
AU - Ohe, Kouichi
PY - 2008/11/21
Y1 - 2008/11/21
N2 - (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.
AB - (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.
UR - http://www.scopus.com/inward/record.url?scp=56449095714&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=56449095714&partnerID=8YFLogxK
U2 - 10.1021/jo801776v
DO - 10.1021/jo801776v
M3 - Article
C2 - 18925786
AN - SCOPUS:56449095714
VL - 73
SP - 9174
EP - 9176
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 22
ER -