97799-86-5

Usage

Structure

A six-membered benzene ring fused to a five-membered nitrogen-containing ring

Appearance

Colorless to light yellow liquid

Odor

Strong, sweet, floral

Usage

Production of fragrances and perfumes, synthesis of pharmaceuticals and other organic compounds

Biological activities

Potential anti-inflammatory and anti-proliferative properties

Upstream product

• 110-89-4 piperidine 
• 65081-41-6 1,2,4,6-tetramethyl-3-nitropyridinium iodide 
• 67-64-1 acetone 
• 6407-34-7 methyl-1 ethylideneamine 
• 109-89-7 diethylamine 
• 124-30-1 1-aminooctadecane 
• 618-36-0 rac-methylbenzylamine 
• 75815-80-4 (1S)-N-(1-methylethylidene)-1-phenylethylamine 
• 124-40-3 dimethyl amine 

Downstream Products

• 1293366-63-8 3-(4-methoxyphenyl)-1,2,4,6-tetramethylindole 

Relevant academic research and scientific papers

STERIC EFFECTS IN THE SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS

In the synthesis of indoles from pyridinium salts the degree of transamination depends on the character of the alkyl group attached to the nitrogen atom of the amine and its nucleophilicity.The yields of indoles decrease as the steric hindrance becomes greater.

Indoles from 3-Nitropyridinium Salts: A new Route to Chiral Indoles and Indolines

(S)-1-(1-Methylbenzyl)-2,4,6-trimethylindole was prepared by interaction of (S)-isopropyliden(1-methylbenzyl)amine with 1,2,4,6-tetramethyl-3-nitropyridinium iodide.The indoles thus prepared undergo diastereoselective hydride reduction and debenzylation to afford chiral (S)-2,4,6-trimethylindoline with high yield an optical purity up to 76percent.

Synthesis of indoles from pyridinium salts. 7. Sterically hindered alkyl-3-nitropyridinium salts in the synthesis of indoles

The introduction of bulky alkyl substituents (iso-Pr,tert-Bu) into any positions of the starting 3-nitropyridinium salt only increases the reaction time and decreases the yields of the corresponding alkylindoles somewhat.

SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS 5. SECONDARY AMINES IN THE REACTION OF 3-NITROPYRIDINIUM SALTS WITH ACETONE

The use of secondary amines in the reaction of 3-nitropyridinium salts with acetone makes it possible to isolate stable intermediates in the formation of indoles - (o-N,N-dialkylaminobenzyl)ketones - and to observe new reaction pathways - the formation of bisindolylpropanes and p-nitroanilines.

SYNTHESIS OF INDOLES FROM PYRIDINIUM SALTS. 4. KETIMINES IN THE SYNTHESIS OF INDOLES FROM 3-NITROPYRIDINIUM SALTS

The possibility of using certain ketimines in place of mixtures of ketone and amine in the synthesis of indoles from 3-nitropyridinium salts has been demonstrated.The use of ketimines leads, in many cases, to increased yields of indoles and simplifies their isolation.It has been established that the rate of indole formation is considerably increased in polar aprotic solvents.