13474-48-1

Usage

Physical state

Yellow crystalline solid

Uses

Organic synthesis, reagent in analytical chemistry, ligand in coordination chemistry, potential pharmacological properties (antimicrobial, anticancer), development of sensors and materials.

Upstream product

• 538-49-8 2-styrylpyridine 
• 1620-53-7 1-phenyl-2-pyridin-2-ylethanone 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 13141-42-9 2-(2-phenylethynyl)pyridine 
• 1121-60-4 pyridine-2-carbaldehyde 
• 27049-45-2 benzyl 2-pyridyl ketone 
• 536-74-3 phenylacetylene 
• 109-04-6 2-bromo-pyridine 
• 2739-97-1 pyridine-2-acetonitrile 
• 10472-94-3 1-phenyl-3-pyridin-2-yl-propane-1,3-dione 
• 613-90-1 benzoyl cyanide 
• 500-22-1 3-pyridinecarboxaldehyde 
• 172265-16-6 2-<(Benzotriazol-1-yl)ethoxymethyl>pyridine 
• 100-52-7 benzaldehyde 

Downstream Products

• 76981-27-6 2-hydroxy-1-phenyl-2-(2-pyridyl)ethanone 
• 92028-61-0 1-phenyl-2-(2-pyridyl)-1,2-ethanediol 
• 1233251-20-1 2-phenyl-3-pyridin-2-yl-5,7-di-2-thienylthieno[3,4-b]pyrazine 

Relevant academic research and scientific papers

Facile aerobic photo-oxidative synthesis of α-diketones from alkynes

We report a useful method for facile aerobic photo-oxidative synthesis of α-diketones from alkynes with MgBr2·OEt2. This procedure provides a practical synthetic method of α-diketones using easily handled bromine sources, harmless visible light, and molecular oxygen as terminal oxidant.

Gold-Catalyzed Oxidation of Internal Alkynes into Benzils and its Application for One-Pot Synthesis of Five-, Six-, and Seven-Membered Azaheterocycles

Internal alkynes have been shown to undergo oxidation to substituted benzils (1,2-diarylethane-1,2-diones) by α-picoline N-oxide in the presence of Ph3PAuNТf2 (5 mol-%). In addition to the unsubstituted benzil, the method allows preparing, under markedly mild conditions (50 °C in chlorobenzene), various non-symmetrical products, including heteroaromatic versions thereof which are much more difficult to obtain otherwise. This gold(I)-catalyzed transformation was integrated into one-pot reaction sequence delivering a range of 5- to 7-membered ring systems (imidazoles, quinoxalines, 1,2,4-triazines, pyrazines, and 1,4-diazepines), thus linking these important heterocyclic motifs to the internal alkyne reagent space.

Metal-Free Iodine-Catalyzed Oxidation of Ynamides and Diaryl Acetylenes into 1,2-Diketo Compounds

Metal-free oxidation of ynamides is described, employing pyridine-N-oxides as oxidants under molecular iodine catalysis. In stark contrast to Br?nsted acid catalysis, iodophilic activation of ynamides diverts the reaction manifold into a dioxygenation pathway. This oxidation is very rapid at room temperature with only 2.5 mol % I2. Furthermore, this protocol could be extended to nonactivated alkynes, such as diarylacetylenes, to deliver various benzil derivatives.

Two-Step One-Pot Synthesis of Unsymmetrical (Hetero)Aryl 1,2-Diketones by Addition-Oxygenation of Potassium Aryltrifluoroborates to (Hetero)Arylacetonitriles

An efficient one-pot two-step procedure for the synthesis of unsymmetrical (hetero)aryl 1,2-diketones has been developed. The reaction proceeds through a palladium-catalyzed nucleophilic addition of potassium aryltrifluoroborates to aliphatic nitriles followed by a copper-catalyzed aerobic benzylic C–H oxygenation using molecular oxygen as a green oxidant. This represents the first example of the direct synthesis of unsymmetrical diaryl 1,2-diketones from arylacetonitriles. This method utilizes inexpensive, stable, nontoxic, and readily available starting materials, is highly effective in the presence of both electron-rich and electron-poor nitriles and aryltrifluoroborates, and tolerates a wide variety of functional groups. The synthetic utility of this transformation was shown by increasing the scale of the reaction and by carrying out the one-pot protocol for the preparation of quinoxaline and benzimidazole derivatives. A plausible reaction mechanism has also been proposed.

Copper-catalyzed TEMPO oxidative cleavage of 1,3-diketones and β-keto esters for the synthesis of 1,2-diketones and α-keto esters

A copper-catalyzed efficient and practical method has been developed for the synthesis of 1,2-diketones and α-keto esters. TEMPO was used as a radical initiator and scavenger, oxidizing the cleavage of α-methylene of 1,3-diketones and β-keto esters to form 1,2-diketones and α-keto esters. This method provided a general way for the formation of 1,2-dicarbonyl compounds.

Diversity-Oriented Synthesis of a Library of Star-Shaped 2H-Imidazolines

A library of star-shaped 2H-imidazolines has been synthesized via Debus-Radziszewski condensation from 1,2-diketones and ketone starting materials. Selective reduction of one imine group of the 2H-imidazole intermediate with LiAlH4 or catalytic flow hydrogenation furnished 2H-imidazolines, which could be conveniently diversified by reacting the amine N with electrophiles, resulting in a set of 21 amide-, carbamate-, urea-, and allylamine-containing products. In total, five points of diversification could be used, which allow the production of a set of functionally diverse compounds. The synthesis of acylated 2H-imidazolidines resulted in intrinsically labile compounds, which spontaneously degraded to acyclic derivatives, as shown for the reaction of 2H-imidazolidine with hexylisocyanate.

Synthesis of α,β-diketotriazoles by aerobic copper-catalyzed oxygenation with triazole as an intramolecular assisting group

The catalytic oxidation of α-ketotriazoles to α,β- diketotriazoles was performed with CuCl2 or CuI/2,9-dimethyl-1,10- phenanthroline in air at 80 °C in good yields. Studies showed that the triazole group participates in complexation to the copper and favors oxidation. Copyright

Pyridine N-oxide mediated oxidation of diarylalkynes with palladium on carbon

Pyridine N-oxide works as an effective oxidant of 1,2-diarylalkynes at 120 °C to form benzil derivatives under Pd/C-catalyzed solvent-free conditions, and Pd/C could be reused up to five times after simple filtration.

Polymer-supported synthesis of α- and β-hydroxyketones through the formation of 1,3-dithiane intermediates

The synthesis of polymer-supported 2-monosubstituted 1,3-dithianes from soluble copolymers bearing 1,3-propanedithiol groups, their lithiation, reactions with electrophiles such as aldehydes, ketones, α,β- unsaturated ketones and oxiranes, and cleavage of

The methyl group as a source of structural diversity in heterocyclic chemistry: Side chain functionalization of picolines and related heterocycles

(Chemical Equation Presented) The reaction of 2-picoline at the methyl group with NDA and KDA followed by dimethyldisulfide trapping furnished, respectively, dithioacetals and trithioortho esters with high selectivity. The method was successfully applied to other methyl-substituted pyridines, quinolines, and pyrazines. Dithioketals were prepared by a one-pot procedure involving the reaction of metalated 2-picoline with 2 equiv of dimethyldisulfide followed by in situ trapping with a second electrophile. All of the generated thio-substituted compounds were efficiently transformed in presence of mercury salts or under oxidizing conditions to other functional groups comprising aldehydes, ketones, ketals, thiol esters, orthoesters, and esters.