146495-33-2

Usage

Chemical structure

Contains an amino group, nitro group, two methoxy groups, and a phenyl ring

Potential pharmacological properties

Due to its functional groups

Applications

Possible use in pharmaceutical drug development or medicinal chemistry research

Upstream product

• 17354-04-0 2-(4,5-dimethoxy-2-nitrophenyl)acetonitrile 
• 185-80-8 1-oxa-2-azaspiro[2.5]octane 

Relevant academic research and scientific papers

Electrophilic Amination of C-H-Acidic Compounds with 1-Oxa-2-azaspirooctane

The reactions of 1-oxa-2-azaspirooctane (1, 3,3-pentamethyleneoxaziridine) with malonic (e. g. 4, 35) and cyanoacetic acid derivatives (e. g. 11, 13, 20) and other C-H acids have been studied.After the introduction of a 1-hydroxycyclohexylamino group at the acidic position, five different stabilisation reactions of the intermediate 2 could be classified.The most important one is an intramolecular nucleophilic attack to a nitrile group giving disubstituted 1,4-diazaspiro decanones 2a.Their ring transformations (e. g. 2a -> 3) or the introduction of a second amino group at the same carbon atom (2a -> 3a) are further new reactions.Geminal diamino acid derivatives 3a thus obtained can be stable or rearrange to 3 (R1 = NH2) or eliminate cyclohexanone (formation of 42) and/or ammonia (formation of 41 or 43).Amination of N-cyanoacetyl-protected amino acid esters (20, NHR = amino acid unit) with 1 yields cyclic dipeptide derivatives 41. Key Words: 1-Oxa-2-azaspirooctane / C-H acids / Electrophilic amination / Diamination / Amino acid derivatives / Dehydro peptides