20531-89-9

Upstream product

• 4392-24-9 Cinnamyl bromide 
• 127-06-0 acetone oxime 
• 46181-30-0 6-methyl-2-phenylpyridine 
• 144-55-8 sodium hydrogencarbonate 
• 931-19-1 2-methylpyridine N-oxide 
• 591-50-4 iodobenzene 
• 98-80-6 phenylboronic acid 
• 100047-37-8 6-Nitro-2-picoline-N-oxide 
• 100-58-3 phenylmagnesium bromide 
• 1824-81-3 2-Amino-6-methylpyridine 
• 18368-61-1 2-methyl-6-nitropyridine 
• 1131-33-5 2-phenylpyridin N-oxide 
• 75-65-0 tert-butyl alcohol 
• 617-94-7 1-methyl-1-phenylethyl alcohol 

Downstream Products

• 206181-87-5 acetic acid 6-phenyl-pyridin-2-ylmethyl ester 
• 147937-33-5 2-(Chloromethyl)-6-phenylpyridine 
• 134370-43-7 2-<(Diethoxyphosphinyl)methyl>-6-phenylpyridine 
• 162614-73-5 2-phenyl-6-(hydroxymethyl)-pyridine 
• 157402-44-3 6-phenylpyridine-2-carbaldehyde 

Relevant academic research and scientific papers

Transition-Metal-Free Regioselective Alkylation of Quinoline N-Oxides via Oxidative Alkyl Migration and C?C Bond Cleavage of tert-/sec-Alcohols

An unprecedented C2-alkylation of quinoline N-oxide derivatives via C?C bond activation of tert- and sec-alkyl alcohol is described using hypervalent iodine (III) reagent PhI(OAc)2 (PIDA). This regioselective alkylation using mild hypervalent iodine reagents is more practical, operationally simple and transition metal free. The reaction proceeds efficiently with a broad range of substrates including quinoline, isoquinoline, and pyridine N-oxides using a variety of tert-/sec- alcohols. From experimental outcome, we also propose a rationalized mechanism, mediated by PIDA. (Figure presented.).

Pd(II)-catalyzed monoarylation of 2-phenylpyridine N-oxide with iodobenzene in water

A Pd(II)-catalyzed activation and arylation of C(sp2)–H bond directed by pyridine N-oxide in water is achieved with high regioselectivity to form monoarylated products in yields up to 91%. The wide substrate scope highlights the flexibility of the catalyst. The reaction mechanism was proposed and the application of this method was taken as an example by the synthesis of COX-2 inhibitor analog.

Palladium-catalyzed direct C-H arylation of pyridine N-oxides with potassium aryl- and heteroaryltrifluoroborates

An efficient ligand-free Pd(OAc)2-catalyzed selective arylation of pyridine N-oxides using potassium (hetero)aryltrifluoroborates as coupling partners via C-H bond activation was achieved in the presence of TBAI. This approach has a broad subst

Arylation of pyridine N-oxides via a ligand-free Suzuki reaction in water

We report a practical and highly efficient protocol for the arylation of pyridine N-oxides with arylboronic acid through palladium-catalyzed Suzuki reaction in water. This ligand-free Suzuki reaction is performed in the presence of diisopropylamine and gi

Substitution of the nitro group with Grignard reagents: Facile arylation and alkenylation of pyridine N-oxides

The unprecedented substitution of a nitro group with aryl or alkenyl groups of Grignard reagents affords 2-aryl or alkenylpyridine N-oxides in modest to high yields with high chemoselectivity. This protocol allows a simple and clean synthesis of various 2

Silver-catalyzed 2-pyridyl arylation of pyridine N-oxides with arylboronic acids at room temperature

A novel direct arylation of pyridine N-oxides with arylboronic acids through C-H functionalization has been developed. This new reaction is performed at room temperature using catalytic silver(I) nitrate in the presence of potassium persulfate and give 2-

Inhibition of 1-deoxy-d-xylulose-5-phosphate reductoisomerase by lipophilic phosphonates: SAR, QSAR, and crystallographic studies

1-Deoxy-d-xylulose-5-phosphate reductoisomerase (DXR) is a novel target for developing new antibacterial (including antituberculosis) and antimalaria drugs. Forty-one lipophilic phosphonates, representing a new class of DXR inhibitors, were synthesized, among which 5-phenylpyridin-2-ylmethylphosphonic acid possesses the most activity against E. coli DXR (EcDXR) with a K i of 420 nM. Structure-activity relationships (SAR) are discussed, which can be rationalized using our EcDXR:inhibitor structures, and a predictive quantitative SAR (QSAR) model is also developed. Since inhibition studies of DXR from Mycobacterium tuberculosis (MtDXR) have not been performed well, 48 EcDXR inhibitors with a broad chemical diversity were found, however, to generally exhibit considerably reduced activity against MtDXR. The crystal structure of a MtDXR:inhibitor complex reveals the flexible loop containing the residues 198-208 has no strong interactions with the 3,4-dichlorophenyl group of the inhibitor, representing a structural basis for the reduced activity. Overall, these results provide implications in the future design and development of potent DXR inhibitors.

COPPER-CATALYZED C-H BOND ARYLATION

The present invention is a one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using a combination of aryl halides, a substrate, and a copper salt as catalyst. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores and explosives.

A general method for copper-catalyzed arylation of arene C-H bonds

A general method for copper-catalyzed arylation of sp2 C-H bonds with pKa's below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper-phenanthroline complex intermediates were independently synthesized.

Piperazine and piperidine compounds

A group of new piperazine and piperidine compounds having interesting advantageous pharmacological properties and have the formula (a) wherein A represents a heterocyclic group having 5-7 ring atoms wherein 1-3 heteroatoms selected from the group O, N and