57785-86-1

Upstream product

• 142-08-5 2-Pyridone 
• 98-59-9 p-toluenesulfonyl chloride 
• 29637-85-2 1-tosyl-pyridin-2(1H)-one 
• 142-08-5 2-hydroxypyridin 
• 504-29-0 2-aminopyridine 
• 104-15-4 toluene-4-sulfonic acid 
• 4124-41-8 p-toluenesulfonylanhydride 
• 657-84-1 sodium tosylate 

Downstream Products

• 101-82-6 2-Benzylpyridine 
• 10273-89-9 2-(2-methylphenyl)pyridine 
• 5957-90-4 4-(2-pyridinyl)anisole 
• 21298-55-5 3-(2-pyridyl)thiophene 
• 4253-81-0 2-(2-nitrophenyl)pyridine 
• 51263-32-2 N-2-pyridylcaprolactam 
• 3419-91-8 N-(2-pyridyl)indole 
• 349574-30-7 3-methyl-N-(pyridin-2-yl)butanamide 
• 86847-59-8 2-(pivaloylamino)pyridine 
• 6631-37-4 2-(phenylamino)pyridine 
• 1285695-10-4 (4-(2-hydroxyphenyl)piperazin-1-yl)(pyridin-2-yl)methanone 
• 172138-95-3 N,N'-((1S,2S)-cyclohexane-1,2-diyl)dipicolinamide 
• 1090354-52-1 N-(3-phenylprop-2-yn-1-yl)picolinamide 
• 1158179-21-5 N-(1'-hydroxy-1'-phenylpropan-2'-yl)-N-methylpicolinamide 

Relevant academic research and scientific papers

Highly efficient Diels-Alder cycloadditions of 2-pyridones with bulky N-sulfonyl substituent

The rearrangement of N-sulfonyl pyridones to the corresponding O-sulfonyl pyridinols during cycloaddition can be greatly retarded by introduction of steric congestion on either the pyridone ring or the sulfonyl group. Hence, significantly improved yields

Copper-assisted preparation of pyridinyl sulfonate esters from hydroxypyridines and sodium sulfinates

An efficient and powerful copper-assisted method for the effective conversion of a broad range of hydroxypyridines and sodium sulfinates into their corresponding pyridinyl tosylates was developed. Key features of this base- and ligand-free protocol include using the cheap and readily available CuBr2 as a medium and the use of sodium sulfinates as formal sulfonylation reagents. A variety of functional pyridinyl tosylates could be formed with good yields, which can easily be converted into C-C and C-N bond-containing compounds. This journal is

Coupling of C(sp3)-H bonds with C(sp2)-O electrophiles: mild, general and selective

Herein is reported the mild and general coupling of amine/ether C(sp3)-H bonds with various kinds of C(sp2)-O electrophiles with high selectivity and efficiency. Valuable allylic/benzylic amines are generated in moderate to excellent yields. The utility of this transformation is demonstrated by a broad substrate scope (>50 examples), good functional group tolerance and facile product modification.

Copper-Catalyzed C-S Bond Formation via the Cleavage of C-O Bonds in the Presence of S8 as the Sulfur Source

Useful and applicable methods for one-pot and odorless synthesis of unsymmetrical and symmetrical diaryl sulfides via C-O bond activation are presented. First, a new efficient procedure for the synthesis of unsymmetrical sulfides using the cross-coupling reaction of phenolic esters such as acetates, tosylates, and triflates and with arylboronic acid or triphenyltin chloride as the coupling partners is reported. Depending on the reaction, S 8 /KF or S 8 /NaO t -Bu system is found to be an effective source of sulfur in the presence of copper salts and in poly(ethylene glycol) as a green solvent. Then, the synthesis of symmetrical diaryl sulfides from phenolic compounds by using S 8 as the sulfur source and NaO t -Bu in anhydrous DMF at 120 °C under N 2 is described. By these protocols, the synthesis of a variety of unsymmetrical and symmetrical sulfides become easier than the available protocols in which thiols and aryl halides are directly used for the preparation of the sulfides.

METAL OXIDE CATALYZED RADIOFLUORINATION

Inter alia, the first titania-catalyzed [18F]-radiofluorination in highly aqueous medium is provided. In embodiments, the method utilizes titanium dioxide, 1 : 1 acetonitrile- thexyl alcohol solvent mixture and tetrabutylammonium bicarbonate as a base. Radiolabeling may be directly performed with aqueous [18F]fluoride without the need for drying/azeotroping step, which reduces radiosynthesis time while keeping high fluoride conversion. The general applicability of the synthetic strategy to the synthesis of the wide range of PET probes from tosylated precursors is demonstrated.

A Novel Convenient Synthesis of Pyridinyl and Quinolinyl Triflates and Tosylates via One-Pot Diazotization of Aminopyridines and Aminoquinolines in Solution

The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves diazotization of the heterocyclic amines with sodium nitrite in mixed hexane-DMSO or hexane-DMF solutions in the presence of trifluoromethanesulfonic acid or p-toluenesulfonic acid.

Titania-catalyzed radiofluorination of tosylated precursors in highly aqueous medium

Nucleophilic radiofluorination is an efficient synthetic route to many positron-emission tomography (PET) probes, but removal of water to activate the cyclotron-produced [18F]fluoride has to be performed prior to reaction, which significantly increases overall radiolabeling time and causes radioactivity loss. In this report, we demonstrate the possibility of 18F-radiofluorination in highly aqueous medium. The method utilizes titania nanoparticles, 1:1 (v/v) acetonitrile-thexyl alcohol solvent mixture, and tetra-n-butylammonium bicarbonate as a phase-transfer agent. Efficient radiolabeling is directly performed with aqueous [18F]fluoride without the need for a drying/azeotroping step to significantly reduce radiosynthesis time. High radiochemical purity of the target compound is also achieved. The substrate scope of the synthetic strategy is demonstrated with a range of aromatic, aliphatic, and cycloaliphatic tosylated precursors.

Aminocarbonylation of Aryl Tosylates to Carboxamides

The palladium - catalyzed aminocarbonylation of aryl tosylates with amines is reported. Suitable conditions were identified by high throughput reaction screening and then further optimized. The substrate scope of the reaction with respect to the aryl tosylate component and the amine component are reported. Competitive aminolysis of the aryl tosylates to afford the amine toluenesulfonamides and the phenol was not observed.

A new one-pot solvent-free synthesis of pyridinyl tosylates via diazotization of aminopyridines

A new, convenient, one-pot method for the synthesis of pyridinyl tosylates is developed. The procedure involves sequential diazotization/tosylation of aminopyridines with sodium nitrite and p-toluenesulfonic acid under solvent-free conditions in a water p

Decarboxylative cross-coupling of aryl tosylates with aromatic carboxylate salts

(Figure Presented) A bimetallic copper/palladium catalyst system is disclosed that enables the use of tosylates as carbon electrophiles in decarboxylative coupling reactions. A variety of aromatic carboxylate salts, regardless of their substitution pattern, have been coupled with these inexpensive and readily available electrophiles to give the corresponding biaryl compounds in good yields (see scheme).