17828-67-0

Upstream product

• 591-50-4 iodobenzene 
• 17666-95-4 5-methoxy-1H-indene-1,3(2H)-dione 
• 140-29-4 phenylacetonitrile 
• 5415-11-2 3-(4-methoxyphenyl)-3-oxo-2-phenylpropanenitrile 
• 121-98-2 methyl 4-methoxybenzoate 
• 199987-33-2 3-amino-2-phenyl-5-methoxy-1-indenone 

Relevant academic research and scientific papers

Palladium-Catalyzed Direct α-Arylation of Indane-1,3-dione to 2-Substituted Indene-1,3-diones

A straightforward and feasible palladium-catalyzed direct α-arylation of indane-1,3-dione to 2-substituted aryl/heteroaryl indene-1,3-diones has been disclosed for the first time. Optimization of reaction conditions identified tBu-XPhos as a preferred ligand for the bis(acetonitrile)dichloropalladium(II) catalyst. A broad spectrum of aryl iodides and aryl triflates containing electron-donating, electron-withdrawing, and sterically hindered substituents gave an excellent yield for the quick access α-arylated 1,3-diones library.

INDANONE AND INDANDIONE DERIVATIVES AND HETEROCYCLIC ANALOGS

The invention relates to indanone/indandione derivatives and heterocyclic analogs of Formula (I) wherein Ar1, A, B, L1, Y, Z, and (R1)n n are as described in the description; to pharmaceutically acceptable salts thereof, and to the use of such compounds as medicaments, especially as NPS receptor antagonists.

Enolate Ions as ss-Activators of ortho-metalation: Direct Synthesis of 3-Aminoindenones

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.