1947-47-3Relevant articles and documents
Gold/Lewis acid catalyzed oxidative cyclization involving activation of nitriles
Wang, Ali,Xie, Xin,Zhang, Chunli,Liu, Yuanhong
supporting information, p. 15581 - 15584 (2020/12/30)
A gold-catalyzed oxidative cyclization of alkyne-nitriles using water or alcohol as the external nucleophiles has been developed. The catalytic system, featured with gold and Lewis acid dual catalysis, allows a facile synthesis of functionalized isoquinolin-1(2H)-ones and 1-alkoxy-isoquinolines with a wide structural diversity. This journal is
Enolate Ions as ss-Activators of ortho-metalation: Direct Synthesis of 3-Aminoindenones
Kayaleh, Nadim E.,Gupta, Ramesh C.,Johnson, Francis
, p. 4515 - 4522 (2007/10/03)
ss-Ketonitriles derived from a Claisen condensation of benzoate esters with alkyl- or phenylacetonitriles lead to 3-aminoindenones in the presence of excess LDA. This new reaction is also applicable to pyridine carboxylic esters. All of the 3-aminoindenones and their aza analogues can be hydrolyzed by acid to give the corresponding 1,3-indandiones. The mechanism of the reaction falls into the directed-ortho-metalation class in which the initial enolate ion of the keto-nitrile directs self-metalation at an ortho position. The new anion then cyclizes onto the nitrile group to generate an aminoindenone. Surprisingly the simplest member of the series, benzoylacetonitrile, does not undergo cyclization. Mechanistic isotope studies revealed that this substance preferentially and directly forms a dianion on the side chain, which is not further deprotonated at the ortho position of the aromatic ring.
