1947-47-3

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 87, p. 874, 1965 DOI: 10.1021/ja01082a030

InChI:InChI=1/C15H11NO/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13,16H/b16-14+/t13-/m1/s1

Upstream product

• 83-12-5 phenindione 
• 631-61-8 ammonium acetate 
• 93-89-0 benzoic acid ethyl ester 
• 140-29-4 phenylacetonitrile 
• 5415-07-6 3-oxo-2,3-diphenyl-propionitrile 
• 440361-82-0 2-phenyl-3-(triphenylphosphoranylideneamino)-indan-1-one 
• 85-44-9 phthalic anhydride 
• 40920-46-5 3-chloro-2-phenyl-1-indenone 
• 440361-81-9 3-azido-2-phenylindan-1-one 
• 93-58-3 benzoic acid methyl ester 

Downstream Products

• 40920-46-5 3-chloro-2-phenyl-1-indenone 
• 1953-72-6 2,3-Dichlor-2-phenyl-indan-1-on 
• 3014-48-0 3-Diacetylamino-2-phenyl-indenon 
• 2775-28-2 2,3-Bis-propionyloxy-2-phenyl-indan-1-on 
• 1953-62-4 3-Acetylamino-2-phenyl-indenon 
• 1610362-48-5 1-((3S,4R)-4-(3,4-difluorophenyl)-1-(2-methoxyethyl)pyrrolidin-3-yl)-3-(1-oxo-2-phenyl-1H-inden-3-yl)urea 

Relevant academic research and scientific papers

Gold/Lewis acid catalyzed oxidative cyclization involving activation of nitriles

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

Thermal cyclization of 3-azido-2-phenyl-indan-1-one to 5H-indeno[1,2-b]indol-10-one [1]

3-Azido-2-phenylindan-1-one (4), which was obtained from 3-chloro-2-phenylindan-1-one (3), cyclizes on thermolysis to 5H-indeno[1,2-b]indol-10-one (5). Reaction of 3-azido-2-phenylindan-1-one (4) with triphenylphosphane gives 2-phenyl-3-(triphenylphosphoranylideneamino)-indan-1-one (6), which can be hydrolyzed to 3-amino-2-phenylindan-1-one (7). Attempts to perform a similar cyclization sequence with 3-chloro-2-pyridylindan-1-ones failed.

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.

A new anionic cyclization reaction: Condensation of benzoate esters with nitriles to give 3-amino-2-inden-1-ones

A new type of anionic cyclization has been discovered in which the condensation of alkyl benzoates with simple nitriles, induced by an excess of LDA, leads directly to substituted-3-amino-1-ones. The corresponding intermediate β-oxonitriles undergo cyclization to give, in most instances, superior yields of the same compounds. Acid hydrolysis of these indenones leads in high yield to the corresponding biologically active (anticoagulant) indandiones.