36149-75-4

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 82, p. 3977, 1960 DOI: 10.1021/ja01500a046Journal of Heterocyclic Chemistry, 24, p. 1261, 1987 DOI: 10.1002/jhet.5570240505

Upstream product

• 55116-04-6 1,4-Dihydro-3(2H)-cinnolinone 
• 7647-01-0 hydrogenchloride 
• 2444-36-2 2'-chloro-benzeneacetic acid 
• 31777-46-5 cinnolin-3(2H)-one 
• 66859-80-1 (2-hydrazino-phenyl)-acetic acid 

Downstream Products

• 126554-94-7 1-(p-methylbenzalamino)-2-indolinone 
• 109410-32-4 1-benzalamino-2-indolinone 
• 126554-93-6 1-(p-methoxybenzalamino)-2-indolinone 
• 94594-85-1 (E)-3-(3-Methoxy-phenyl)-3-(2-oxo-2,3-dihydro-indol-1-ylamino)-acrylic acid ethyl ester 
• 59-48-3 2-oxoindole 
• 31777-46-5 cinnolin-3(2H)-one 
• 60230-84-4 2-Phenyl-4H-pyrazolo[1,5-a]indole-3-carboxylic acid 
• 60230-85-5 2(3-methoxyphenyl)-4H-pyrazolo<1,5-a>indole-3-carboxylic acid 
• 94619-45-1 2-Phenyl-4H-pyrazolo[1,5-a]indole-3-carboxylic acid ethyl ester 
• 94619-46-2 ethyl 2(3-methoxyphenyl)-4H-pyrazolo<1,5-a>indole-3-carboxylate 
• 60230-72-0 2-phenyl-4H-pyrazolo<1,5-a>indole 
• 60230-73-1 2(3-methoxyphenyl)-4H-pyrazolo<1,5-a>indole 
• 126555-00-8 2-(p-methoxybenzyl)-3(2H)-cinnolinone 
• 126554-96-9 1-benzylamino-2-indolinone 

Relevant academic research and scientific papers

Copper powder-catalyzed chelation-assisted cascade reaction of: O -chloroarylacetic acids with amines under solvent- and ligand-free conditions: Synthesis of oxindoles

An efficient method to construct oxindole scaffolds from o-chloroarylacetic acids/esters with amines has been explored. This cascade protocol involves the in situ generation of o-aminoarylacetic acid derivatives by the copper powder catalyzed and weak O-chelation assisted Ullmann amination of unactivated C-Cl bonds under air, and solvent-/ligand-free conditions followed by annulative N-acylation.

Reduction Products of 3(2H)-Cinnolinones

Reduction of 3(2H)-cinnolinone with zinc and ammonium hydroxide forms 1,4-dihydro-3(2H)-cinnolinone which rapidly rearranges to 1-amino-2-indolinone (1-aminooxindole) in acid solution. 1,4-Dihydro-2-methyl-3(2H)-cinnolinone is formed from 2-methyl-3(2H)-cinnolinone under the same conditions, but its rearrangement to 1-(N-methylamino)-2-indolinone (1-(N-methylamino)oxindole) in acid solution is much slower.

Rearrangements of N-Nitrenes: a 15N- Labelling Study of the Mechanism of the Conversion of 1-Aminoindol-2-one to Cinnolin-3(2H)-one

The oxidation of 1-aminoindol-2-one to cinnolin-3(2H)-one is shown by 15N labelling to proceed by migration of acyl rather than the aryl group to the exocyclic nitrogen.Two cinnolin-3(2H)-ones were found to extrude carbon monoxide upon flash vacuum pyrolysis giving indazoles.