1912-16-9

Usage

Uses

Used in Organic Synthesis:
Pyridine, 2-methyl-4,6-diphenylis used as a building block for various pharmaceuticals, agrochemicals, and fine chemicals. Its unique structure and reactivity make it an important intermediate for the production of numerous complex compounds.
Used in Pharmaceutical Industry:
Pyridine, 2-methyl-4,6-diphenylis used as a key intermediate in the synthesis of various pharmaceuticals due to its unique structure and reactivity.
Used in Agrochemical Industry:
Pyridine, 2-methyl-4,6-diphenylis used as a building block in the development of agrochemicals, contributing to the production of effective and targeted products.
Used in Chemical Processes:
Pyridine, 2-methyl-4,6-diphenylis used as a solvent and chemical reagent in various chemical processes, facilitating reactions and improving process efficiency.
Used in Research and Development:
Pyridine, 2-methyl-4,6-diphenylis being researched for potential pharmacological applications due to its biological properties, offering opportunities for the discovery of new therapeutic agents.

Upstream product

• 75-18-3 dimethylsulfide 
• 76-05-1 trifluoroacetic acid 
• 71-43-2 benzene 
• 30086-48-7 1-methylamino-2-methyl-4,6-diphenylpyridinium iodide 
• 617-84-5 N-formyldiethylamine 
• 98-86-2 acetophenone 
• 94-41-7 benzalacetophenone 
• 67-64-1 acetone 
• 19433-17-1 acetophenone O-acetyloxime 
• 1896-62-4 (E)-benzalacetone 
• 121-44-8 triethylamine 
• 36298-61-0 3-phenyl-4-benzylideneisoxazol-5(4H)-one 
• 77202-10-9 4-methyl-6-phenyl-1,2,3-triazine 
• 14001-34-4 N-(prop-1-en-2-yl)acetamide 

Downstream Products

• 19625-63-9 2,4-diphenylpicolinic acid 

Relevant academic research and scientific papers

Shape-selective Synthesis of Substituted Pyridine on Zeolite-hosted Monovalent Cobalt

The synthesis of diphenyl methyl pyridine via the cotrimerization of phenyl acetylene and acetonitrile using a novel monovalent cobalt catalyst generated reductively in zeolitic media is described.

NH4I-Triggered [4 + 2] Annulation of α,β-Unsaturated Ketoxime Acetates with N-Acetyl Enamides for the Synthesis of Pyridines

The NH4I-triggered formal [4 + 2] annulation of α,β-unsaturated ketoxime acetates with N-acetyl enamides has been developed. The current protocol employs electron-rich enamides as C2 synthons and enables the efficient and straightforward construction of polysubstituted pyridines in moderate to good yields based on metal-free systems. The reaction tolerates a wide range of functional groups and represents an alternate route toward the synthesis of pyridine derivatives.

Preliminary results of the reaction of cyclotrimerization of phenylacetylene [2+2+2] catalyzed by [(Cp?)Co(Indene)] complex

This work describes the catalytic study of [(Cp?)Co(Ind)] (with Cp?= pentamethylcyclopentadienyl, Ind= Indenyl, (C9H7)) complex in cyclotrimerization of phenylacetylene. From the cylcotrimerization reaction was possible to obtain products such as substituted pyridines 2-methyl-3,5-diphenylpyridine (3), 2-methyl- 4,6-diphenylpyridine (4) and the compound 1,2,4-triphenylbenzene (5) using acetonitrile as solvent. On the other hand, using toluene as solvent under the same working conditions, the product of reaction was 1,3,5-triphenylbenzene (1). Furthermore, by varying the working conditions, the reaction is 90% selective towards the formation of pyridines. In addition, has been appreciated the formation of another product 1,4-diphenilbuta-1,3-diyne (2), which was isolated and characterized by means NMR and GC-Mass spectrometry.

An aminocatalyzed michael addition/Iron-Mediated decarboxylative cyclization sequence for the preparation of 2,3,4,6-Tetrasubstituted pyridines: Scope and mechanistic insights

A novel, scalable strategy for the preparation of 2,3,4,6-tetrasubstituted pyridines is described. This protocol has two steps: an aminocatalyzed addition of ketones to alkylidene isoxazol-5-ones, followed by an iron-mediated decarboxylative cyclization event. Mechanistic insights for both steps are provided based on HRMS-ESI(+) studies.

Synthesis of polysubstituted pyridines from oxime acetates using NH4I as a dual-function promoter

Pyridine formation with oxime acetates as the building blocks under metal-free conditions is described. Ammonium iodide has proved to be a highly efficient promoter for oxime N-O bond reduction and subsequent condensation reactions, whereby it played a dual-function role in the transformation. While the three-component reaction of oxime acetates, benzaldehydes, and 1,3-dicarbonyls proceeded well with the assistance of a stoichiometric amount of ammonium iodide, the condensation of oximes and acroleins was enabled by using a catalytic initiator to afford substituted pyridines. By this protocol, substituted pyridine products were generated in moderate to excellent yields with tolerance towards a broad range of functional groups.

Synthesis of Highly Substituted Pyridines through Copper-Catalyzed Condensation of Oximes and α,β-Unsaturated Imines

A copper-catalyzed condensation reaction of oxime acetates and α,β-unsaturated ketimines to give pyridine derivatives is reported. The reaction features mild conditions, high functional-group compatibility, and high regioselectivity with respect to unsymmetrical oxime acetates, thus allowing the preparation of a wide range of polysubstituted pyridines, many of which are not readily accessible by conventional condensation methods.

Route to Highly Substituted Pyridines

Pyridine rings are common structural motifs found in a number of biologically active compounds, including some top-selling pharmaceuticals. We have developed a new approach to access substituted pyridines. The method aims to provide a reliable synthesis of a diverse range of substituted pyridines through a three-step procedure. Readily available enones are first converted into 1,5-dicarbonyls through a two-step Hosomi-Sakurai allylation/oxidative cleavage sequence, which is followed by subsequent cyclization to the corresponding pyridine using hydroxylamine hydrochloride. A variety of substituted pyridines have been synthesized using this method.

Metal-Free Assembly of Polysubstituted Pyridines from Oximes and Acroleins

Transition-metal-catalyzed synthesis of N-heterocycles from oximes has been previously well established. In this paper, for the first time a metal-free protocol with the combinational employment of iodine and triethylamine has been demonstrated to be effective to trigger the oxime-based synthesis of pyridines with high chemo-selectivity and wide functional group tolerance. A broad range of functional pyridines were prepared in moderate to excellent yields. While neither iodine nor triethylamine could trigger this transformation, mechanistic experiments indicated a radical pathway for the reaction. The resultant 2-aryl-substituted pyridines have been proved to be versatile building blocks in a range of transition-metal-catalyzed C-H functionalization reactions. (Chemical Equation Presented).

Iron-Catalyzed Cyclization of Ketoxime Carboxylates and Tertiary Anilines for the Synthesis of Pyridines

A novel and efficient iron-catalyzed cyclization of ketoxime carboxylates and N,N-dialkylanilines for the modular synthesis of diverse pyridines was developed. The reaction was initiated by Fe-catalyzed N-O bond cleavage of ketoxime carboxylates in the presence of tertiary anilines. The methylene carbon on N,N-dialkylanilines functioned as a source of one-carbon synthon in the reaction. The reaction used readily available starting materials, tolerated various functional groups, and afforded 2,4-disubstituted and 2,4,6-trisubstituted pyridines in good to high yields under mild conditions.