76228-07-4

Upstream product

• 812647-60-2 3-(1-oxo-2,3-dihydro-1H-benzo[f]quinolin-4-yl)-propionitrile 
• 105901-38-0 3-(2-naphthylamino)propanoic acid 
• 343222-18-4 N-[2]naphthyl-β-alanine ethyl ester 
• 91-59-8 naphthalen-2-ylamine 
• 38266-46-5 3-(2-naphthylamino)propionitrile 
• 76228-04-1 1-Naphthalen-2-yl-azetidin-2-one 

Downstream Products

• 112634-88-5 1-Phenyl-4,5-dihydro-1H-benzo[f]pyrazolo[4,3-c]quinoline-3-carboxylic acid ethyl ester 
• 112634-87-4 1-Phenyl-4,5-dihydro-1H-benzo[f]pyrazolo[4,3-c]quinoline 

Relevant academic research and scientific papers

Synthesis of Benzoquinolinoisoxazoles and Benzoquinolinopyrazoles

1-Oxo-2,3-dihydro-1H-benzo- and 1-acetyl-4-oxo-2,3-dihydro-4H-benzo-quinolines (1 and 2) have been synthesised starting from 2-naphthylamine and 1-acetamidonaphthalene, respectively.Reaction of diethyl oxalate or formylation of these compounds followed by treatment with reagents like hydroxylamine hydrochloride, hydrazine hydrate, phenylhydrazine, semicarbazide hydrochloride, thiosemicarbazide hydrochloride lead to isoxazole and pyrazole fused benzo- and benzo-quinolines (4,8 and 5,9 respectively).

Formation of 2,3-Dihydro-4(1H)-quinolones and Related Compounds via Fries-type Acid-catalysed Rearrangement of 1-Arylazetidin-2-ones

A variety of 1-arylazetidin-2-ones were treated with trifluoroacetic acid under reflux, methanesulphonic acid at 100 deg C, or conc. sulphuric acid to give the corresponding 2,3-dihydro-4(1H)-quinolones via acyl migration and N-CO fission.In the case of 1-(3-substituted phenyl)azetidin-2-ones, two positional isomeric products, 5- and 7-substituted 2,3-dihydro-4(1H)-quinolones were obtained. 4-Methyl, 4-ethoxycarbonyl, and 4-piperidin-2-yl-1-arylazetidin-2-ones and their analogues were also converted into the corresponding 2-substituted 2,3-dihydro-4(1H)-quinolones under acidic conditions.The 3-substituted 1-phenylazetidin-2-ones (36) and (37) were converted into the furoquinoline systems (38) and (40), respectively, by application of this method.