209798-50-5

Usage

Uses

Used in Pharmaceutical Industry:
3-Pyridinamine, 2-(2-phenylethenyl)is used as a key building block for the synthesis of various pharmaceuticals. Its antimicrobial, antifungal, and antihistamine properties make it a valuable component in the development of drugs targeting a range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Pyridinamine, 2-(2-phenylethenyl)serves as an essential intermediate in the creation of compounds designed to protect crops and enhance agricultural productivity, leveraging its antimicrobial and antifungal characteristics.
Used in Fine Chemicals Production:
3-Pyridinamine, 2-(2-phenylethenyl)is utilized as a reactive and stable intermediate in the manufacturing of fine chemicals, contributing to the development of high-quality specialty products.
Used in Dye Manufacturing:
3-Pyridinamine, 2-(2-phenylethenyl)is also used in the production of dyes and other organic compounds, capitalizing on its reactivity and stability to create a diverse array of colorants for various applications.

Upstream product

• 100-42-5 styrene 
• 6298-19-7 2-chloro-3-aminopyridine 
• 39856-58-1 3-amino-2-bromopyridine 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 947330-58-7 3-nitro-2-(phenylethynyl)pyridine 
• 536-74-3 phenylacetylene 
• 209286-96-4 2-iodo-3-nitropyridine 

Relevant academic research and scientific papers

Exploiting Iminoquinones as Electrophilic at Nitrogen "n+" Synthons for C-N Bond Construction

New methods for C-N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.

Gold(i)-catalyzed synthesis of 2-substituted indoles from 2-alkynylnitroarenes with diboron as reductant

An efficient method for the synthesis of 2-substituted indoles via a diboron/base promoted tandem reductive cyclization of o-alkynylnitroarene under Au catalysis conditions has been disclosed. This reaction is efficient and convenient, affording 2-substituted indoles with broad functional groups tolerance and excellent yields.

Selenium-catalyzed oxidative c(sp2)-h amination of alkenes exemplified in the expedient synthesis of (Aza-)indoles

A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp2)-N bonds in high yields and with excellent functional group tolerance.

Synthesis of 3-aminopyridine-2-carboxaldehyde thiosemicarbazone (3-AP)

Palladium-catalyzed cross-coupling of methylboronic acid with 2-chloro- 3-nitropyridine produced 2-methyl-3-nitropyridine 4 in one step in high yield. Oxidation of 4 with selenium dioxide gave aldehyde 5. Alternatively, condensation of 4 with DMFDMA followed by oxidation gave 5 in a two step higher yielding conversion. Subsequent direct coupling of 5 with thiosemicarbazide followed by reduction of the nitro group using stannous chloride or sodium sulfide provided 3-AP (3). Reduction with sodium hydrosulfite gave 3-HAP (8). Finally a route which avoids the reduction of a nitro function was devised. Thus direct coupling of styrene with 2-chloro-3- aminopyridine 9 under Heck reaction conditions gave 16 which was converted to 17, oxidized to the aldehyde 18 and converted to 3-AP (3) with in situ deblocking of the t-Boc functionality.