15825-89-5

Upstream product

• 15031-77-3 2-(3-pyridinyl)-2-propanol 
• 626-60-8 3-Chloropyridine 
• 108-22-5 Isopropenyl acetate 
• 350-03-8 methyl-3-pyridylketone 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 626-55-1 3-Bromopyridine 
• 75-24-1 trimethylaluminum 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 93-60-7 methyl 3-pyridinecarboxylate 
• 7664-93-9 sulfuric acid 
• 64-19-7 acetic acid 
• 54-36-4 metyrapone 
• 557-93-7 2-bromoprop-1-ene 
• 89878-14-8 3-Diethylboranylpyridine 

Downstream Products

• 38031-78-6 3-tert-butylpyridine 
• 350-03-8 methyl-3-pyridylketone 
• 1308661-37-1 2-(pyridin-3-yl)-1-tosylpropan-2-ol 

Relevant academic research and scientific papers

Synthesis of N-Alkylpyridin-4-ones and Thiazolo[3,2- a]pyridin-5-ones through Pummerer-Type Reactions

N-Alkylated 4-pyridones were obtained through a one-pot procedure involving either normal or interrupted Pummerer reactions between triflic anhydride-activated sulfoxides and 4-fluoropyridine derivatives, followed by hydrolysis. On the other hand, triflic anhydride-activated benzyl 6-fluoro-2-pyridyl sulfoxide could react with alkenes or alkynes to afford thiazolo[3,2-a]pyridin-5-ones, via the pyridinium salt intermediates.

Synthesis of a Series of Structurally Diverse MB327 Derivatives and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor

A novel series of 30 symmetric bispyridinium and related N-heteroaromatic bisquaternary salts with a propane-1,3-diyl linker was synthesized and characterized for their binding affinity at the MB327 binding site of nicotinic acetylcholine receptor (nAChR) from Torpedo californica. Compounds targeting this binding site are of particular interest for research into new antidotes against organophosphate poisoning, as therapeutically active 4-tert-butyl-substituted bispyridinium salt MB327 was previously identified as a nAChR re-sensitizer. Efficient access to the target compounds was provided by newly developed methods enabling N-alkylation of sterically hindered or electronically deactivated heterocycles exhibiting a wide variety of functional groups. Determination of binding affinities toward the MB327 binding site at the nAChR, using a recently developed mass spectrometry (MS)-based Binding Assay, revealed that several compounds reached affinities similar to that of MB327 (pKi=4.73±0.03). Notably, the newly prepared lipophilic 4-tert-butyl-3-phenyl-substituted bispyridinium salt PTM0022 (3 h) was found to have significantly higher binding affinity, with a pKi value of 5.16±0.07, thus representing considerable progress toward the development of more potent nAChR re-sensitizers.

Expedient synthesis of gem-dialkylbenzyl heterocycles through olefinic hydroarylation

A robust approach to gem-dialkylbenzyl heterocycles has been developed through a triflic acid-catalyzed hydroarylation of olefinic heterocycles. A broad range of substrates containing pyridine, quinoline, pyrazole, triazole and imidazole moieties are shown to be highly compatible with this method. This rapid construction of gem-dialkyl groups should be useful in the synthesis of drug-like molecules containing heterocyclic diversity and in the study of the gem-dialkyl effect.

Iron-Catalyzed Cross-Coupling of Alkenyl Acetates

Stable C-O linkages are generally unreactive in cross-coupling reactions which mostly employ more electrophilic halides or activated esters (triflates, tosylates). Acetates are cheap and easily accessible electrophiles but have not been used in cross-couplings because the strong C-O bond and high propensity to engage in unwanted acetylation and deprotonation. Reported herein is a selective iron-catalyzed cross-coupling of diverse alkenyl acetates, and it operates under mild reaction conditions (0 C, 2 h) with a ligand-free catalyst (1-2 mol%). Iron clad: Acetates are underutilized electrophiles in metal-catalyzed cross-coupling reactions because of the strong alkenyl C-O bond and their propensity to engage in unwanted reactions. Combination of a ligand-free low-valent Fe catalyst with nucleophilic organomagnesium reagents, low temperature, and short reaction times results in highly selective cross-couplings with alkenyl acetates.

Access to "friedel-Crafts-Restricted" tert -alkyl aromatics by activation/methylation of tertiary benzylic alcohols

Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.

FUNGICIDAL ISOXAZOLIDINES

Disclosed are compounds of Formula 1, including all geometric and stereoisomers, N-oxides, and salts thereof, wherein A, B, D, R1, R2, R3, X and m are as defined in the disclosure. Also disclosed are compositions containin

Cobalt-catalyzed vinylation of functionalized aryl halides with vinyl acetates

A new method for the preparation of styrene derivatives is described on the basis of the activation of aryl halides by low-valent cobalt species. A combination of CoII bromide and 2,2′-bipyridine is suitable as catalyst for the cross-coupling reaction of a wide range of aromatic halides (X = Cl, Br, I), mostly bearing sensitive moieties, with vinyl acetates. These reactions proceed under mild conditions in the presence of the appropriate reducing agent to afford α-substituted styrene compounds in satisfactory to high yields. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005.

Cobalt-catalyzed electrochemical vinylation of aryl halides using vinylic acetates

The electroreduction of aryl halides (bromides or chlorides) allows the coupling reaction with vinylic acetates, in the presence of 2,2-bipyridine and catalytic amounts of cobalt bromide, leading to styrene derivatives in good yields.

The photochemistry of metyrapone

Metyrapone undergoes efficient α-cleavage via the n0?* triplet.The fate of the resulting acyl and alkyl radicals has been determined by transient studies as well as through the isolation of the final products, quantum yield measurements and trapping studies.Processes previously documented for carbocyclic analogues of 1, such as disproportionation and coupling of the alkyl radicals and recombination to the starting compound are here accompanied by another major process, viz. coupling with attack of the acyl radical on the pyridine ring, which eventually leads mainly to a polymeric material.

A NOVEL SYNTHESIS OF 3- AND 4-ALKENYLPYRIDINES

A new approach for the simple preparation of 3- and 4-alkenylpyridines that relys upon the palladium catalyzed cross coupling reaction of diethylpyridylboranes with vinylic bromides is described.