74588-82-2

Upstream product

• 74588-91-3 1-phenacylindole-2,3-dione 
• 4636-16-2 iodoacetophenone 
• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 124-41-4 sodium methylate 
• 16120-49-3 spiro[indole-3,2'-oxiran]-3'-benzoyl-2(1H)-one 
• 91-56-5 indole-2,3-dione 
• 17617-34-4 (2‐aminophenyl)oxoacetic acid sodium salt 
• 3342-78-7 2-(2-aminophenyl)acetic acid 
• 70-11-1 α-bromoacetophenone 
• 859068-01-2 (2-oxo-indolin-3-yl)-phenyl-ethanedione 
• 7732-18-5 water 

Downstream Products

• 1022-86-2 2-benzoylindole 
• 83749-67-1 4-Phenyl-2,5-dihydro-pyridazino[4,5-b]indol-1-one 
• 83749-78-4 1-Chloro-4-phenyl-5H-pyridazino[4,5-b]indole 

Relevant academic research and scientific papers

Polyfunctional 4-quinolinones. Synthesis of 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines

We present here two new methods based on rearrangement reactions to obtain novel 2-substituted 3-hydroxy-4-oxo-1,4-dihydroquinolines, an important family of heterocycles with potential applications. Alkyl 3-hydroxy-4-oxo-1,4-dihydroquinoline-2-carboxylates were obtained by alkoxide promoted rearrangement of alkyl isatinacetates. A second synthetic route involves the alkoxide promoted reaction of both isatin and N-methylisatin, with alkylating agents having acidic methylenes. This reaction leads to the formation of spiroepoxyoxindoles via Darzens' condensation. When phenacyl bromides are used, the initially obtained benzoyl substituted spiroepoxyoxindoles were smoothly transformed into the corresponding 2-benzoyl-3-hydroxy-4-quinolinones with good to excellent yields.

Direct N-alkylation of isatin by halomethyl ketones

Solid-phase syntheses are reported for 1-(2-oxoalkyl)indoline-2,3-diones. 2005 Springer Science+Business Media, Inc.

Syntheses of 1-alkyl-2-acylindoles, 1-alkyl-2-acylindole-3-carboxylic acids, and their esters, in superbasic media

2-Acylindoles and 2-acylindole-3-carboxylic acids are readily alkylated at the nitrogen atom by haloalkanes in a superbasic medium (DMSO + NaOH). For the carboxylic acids, this reaction may proceed either entirely at the nitrogen atom, or at both the the

Syntheses of 1-(3-oxoalkyl)indole-2-3-diones

Hydration of the triple bond in 1-(alkyn-2-yl)indole-2,3-diones under Kucherov reaction conditions takes place under the orienting influence of the nitrogen atom with formation of an oxo group exclusively at the γ-carbon atoms. 1996 Plenum Publishing Corporation.

Prototropic Generation of Dipoles. A New Synthesis of Indole-3-carboxylic Acids

Imines of (2-aminophenyl)acetic acid give 2-substituted indole-3-carboxylic acids under mild conditions; the cyclisation is thought to involve a 1,5-dipole and initially to give the corresponding indolines.

A Simple Synthesis of 2-Acyl Indoles from Isatins

N-Phenacyl- and N-acetonyl-isatins can be prepared and converted by treatment with sodium hydroxide into 2-acyl indoles and/or 2-acyl indole-3-carboxylic acids.