3783-38-8

Usage

Uses

Used in Pharmaceutical Industry:
METHYLISONICOTINATE-N-OXIDE is used as an intermediate compound for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, particularly those targeting specific diseases or conditions.
Used in Chemical Synthesis:
In the field of chemical synthesis, METHYLISONICOTINATE-N-OXIDE is used as a building block for creating more complex molecules. Its versatile structure makes it a valuable asset in the development of new compounds with specific properties and applications.
Used in Research and Development:
METHYLISONICOTINATE-N-OXIDE is also utilized in research and development for its potential applications in various scientific fields. Its unique properties make it an interesting subject for further study and exploration, potentially leading to new discoveries and innovations.

InChI:InChI=1/C7H7NO3/c1-11-7(9)6-2-4-8(10)5-3-6/h2-5H,1H3

Upstream product

• 67-56-1 methanol 
• 13602-12-5 Isonicotinic acid N-oxide 
• 16357-59-8 N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline 
• 55-22-1 pyridine-4-carboxylic acid 
• 2459-09-8 4-pyridinecarboxylic acid, methyl ester 

Downstream Products

• 6975-73-1 1-oxide pyridine-4-carbohydrazide 
• 58481-11-1 methyl 2-chloroisonicotinate 
• 89937-77-9 methyl 2-hydroxypyridine-4-carboxylate 
• 1174000-61-3 4-(methoxycarbonyl)-2,6-bis(4-(trifluoromethyl)phenyl)pyridine 1-oxide 
• 94413-64-6 2-Cyano-4-carbomethoxypyridine 
• 1367126-53-1 C₁₈H₁₄FNO₂ 
• 1367126-51-9 C₁₉H₁₄FNO₃ 
• 1367127-23-8 C₂₀H₁₃FN₂O₃ 
• 1367127-25-0 C₁₉H₁₃FN₂O₂ 
• 1367127-27-2 C₂₆H₁₉FN₂O₄S 
• 1367127-30-7 C₂₈H₂₉FN₄O₃ 
• 1367127-32-9 C₂₈H₃₁FN₄O₄ 
• 1367127-34-1 C₂₉H₃₃FN₄O₄ 
• 1367127-21-6 C₁₉H₁₄FNO₄ 

Relevant academic research and scientific papers

Controlling the optical and catalytic properties of artificial metalloenzyme photocatalysts using chemogenetic engineering

Visible light photocatalysis enables a broad range of organic transformations that proceed via single electron or energy transfer. Metal polypyridyl complexes are among the most commonly employed visible light photocatalysts. The photophysical properties of these complexes have been extensively studied and can be tuned by modifying the substituents on the pyridine ligands. On the other hand, ligand modifications that enable substrate binding to control reaction selectivity remain rare. Given the exquisite control that enzymes exert over electron and energy transfer processes in nature, we envisioned that artificial metalloenzymes (ArMs) created by incorporating Ru(ii) polypyridyl complexes into a suitable protein scaffold could provide a means to control photocatalyst properties. This study describes approaches to create covalent and non-covalent ArMs from a variety of Ru(ii) polypyridyl cofactors and a prolyl oligopeptidase scaffold. A panel of ArMs with enhanced photophysical properties were engineered, and the nature of the scaffold/cofactor interactions in these systems was investigated. These ArMs provided higher yields and rates than Ru(Bpy)32+ for the reductive cyclization of dienones and the [2 + 2] photocycloaddition between C-cinnamoyl imidazole and 4-methoxystyrene, suggesting that protein scaffolds could provide a means to improve the efficiency of visible light photocatalysts.

A Photosensitizer-Free Radical Cascade for Synthesizing CF3-Containing Polycyclic Quinazolinones with Visible Light

Herein, we report an efficient photoinduced radical tandem trifluoromethylation/cyclization reaction of N-cyanamide alkenes for the synthesis of functionalized quinazolinones. Importantly, the reaction is carried out under mild conditions without any addi

Visible-Light-Induced ortho-Selective Migration on Pyridyl Ring: Trifluoromethylative Pyridylation of Unactivated Alkenes

The photocatalyzed ortho-selective migration on a pyridyl ring has been achieved for the site-selective trifluoromethylative pyridylation of unactivated alkenes. The overall process is initiated by the selective addition of a CF3 radical to the alkene to provide a nucleophilic alkyl radical intermediate, which enables an intramolecular endo addition exclusively to the ortho-position of the pyridinium salt. Both secondary and tertiary alkyl radicals are well-suited for addition to the C2-position of pyridinium salts to ultimately provide synthetically valuable C2-fluoroalkyl functionalized pyridines. Moreover, the method was successfully applied to the reaction with P-centered radicals. The utility of this transformation was further demonstrated by the late-stage functionalization of complex bioactive molecules.

Photoredox generation of the trifluoromethyl radical from borate complexes: Via single electron reduction

A method for the generation of the CF3 radical from CF3-substituted borate complexes bearing a pyridine-N-oxide ligand is described. Cleavage of the C-B bond occurs via single electron reduction by a Cu(i) photocatalyst activated by visible light.

A combination of flow and batch mode processes for the efficient preparation of mGlu2/3 receptor negative allosteric modulators (NAMs)

Benzodiazepinones are privileged scaffolds with activity against multiple therapeutically relevant biological targets. In support of our ongoing studies around allosteric modulators of metabotropic glutamate receptors (mGlus) we required the multigram synthesis of a β-ketoester key intermediate. We report the continuous flow synthesis of tert-butyl 3-(2-cyanopyridin-4-yl)-3-oxopropanoate and its transformation to potent mGlu2/3 negative allosteric modulators (NAMs) in batch mode.

Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts

We report the first reductive coupling of unactivated alkenes with N-methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts under hydrogen atom transfer (HAT) conditions, and an expanded scope for the coupling of alkenes with N-methoxy pyridinium salts. N-Methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts are accessible in 1-2 steps from the commercial arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from commercial amines (50-85%). In total 36 discrete methoxyheteroarenium salts bearing electron-donating, electron-withdrawing, alkyl, aryl, halogen, and haloalkyl substituents were prepared (several in multigram quantities) and coupled with 38 different alkenes. The transformations proceed under neutral conditions at ambient temperature, provide monoalkylation products exclusively, and form a single alkene addition regioisomer. Preparatively useful and complementary site selectivities in the addition of secondary and tertiary radicals to pyidinium salts are documented: harder secondary radicals favor C-2 addition (2->10:1), while softer tertiary radicals favor bond formation to C-4 (4.7->29:1). A diene possessing a 1,2-disubstituted and 2,2-disubstituted alkene undergoes hydropyridylation at the latter exclusively (61%) suggesting useful site selectivities can be obtained in polyene substrates. The methoxypyridinium salts can also be employed in dehydrogenative arylation, borono-Minisci, and tandem arylation processes. Mechanistic studies support the involvement of a radical process.

Solvent- and halide-free synthesis of pyridine-2-yl substituted ureas through facile C-H functionalization of pyridine: N -oxides

A novel solvent- and halide-free atom-economical synthesis of practically useful pyridine-2-yl substituted ureas utilizes easily accessible or commercially available pyridine N-oxides (PyO) and dialkylcyanamides. The observed C-H functionalization of PyO is suitable for the good-to-high yielding synthesis of a wide range of pyridine-2-yl substituted ureas featuring electron donating and electron withdrawing, sensitive, or even fugitive functional groups at any position of the pyridine ring (63-92%; 19 examples). In the cases of 3-substituted PyO, the C-H functionalization occurs regioselectively providing a route for facile generation of ureas bearing a 5-substituted pyridine-2-yl moiety.

New topiroxostat synthesis intermediate and preparation method thereof

The present invention provides a new topiroxostat synthesis intermediate 4-(2-(imino(pyridine-4-yl)methyl)hydrazinocarbonyl)pyridine N-oxide (compound VI) and a preparation method thereof, wherein isoniazid N-oxide IV and 4-cyanopyridine V are subjected to a reaction in a suitable solvent under an alcohol alkali condition to obtain the product, the alcohol alkali is selected from sodium methoxide, sodium ethoxide, potassium ethoxide or potassium t-butoxide, and the reaction formula is defined in the specification. According to the present invention, through the compound VI, the gout treating drug topiroxostat can be prepared under the mild and easy industrial control reaction conditions.

A method for synthesizing holds the pyrrole department he (by machine translation)

The present invention provides a method for the synthesis of I he holds the pyrrole department, comprising the following steps: 1), II to isonicotinic acid methyl ester as the raw material, the presence of the oxidizing agent, is generated by the oxidation of isonicotinic acid methyl ester N-oxide III; 2), then condensation with hydrazine hydrate to obtain retozide N-oxide IV; 3), compound IV with 4-cyanopyridine mellow alkali V under the conditions of the reaction to produce 4 - (2 - (imino (pyridin-4-yl) methyl) [...] ) pyridine N-oxide VI; 4), the presence of the dimethyl carbamic chloride, and cyanide reaction to produce 2-cyano-Nˊ - (imino (pyridin-4-yl) methyl) retozide VII; 5), the resulting compound in the presence of an acid VII to cyclization, I have he holds the pyrrole department ; the reaction route is as follows: In the method of the invention, the total yield, on the one hand relative to the literature yield greatly improved, on the other hand, line is simple and easy to obtain the raw materials and low cost, the steps of the mild reaction conditions, the post-processing is simple; it is very easy to be industrialized control. (by machine translation)

Selective inhibition of prolyl 4-hydroxylases by bipyridinedicarboxylates

Abstract Collagen is the most abundant protein in animals. A variety of indications are associated with the overproduction of collagen, including fibrotic diseases and cancer metastasis. The stability of collagen relies on the posttranslational modification of proline residues to form (2S,4R)-4-hydroxyproline. This modification is catalyzed by collagen prolyl 4-hydroxylases (CP4Hs), which are Fe(II)- and α-ketoglutarate (AKG)-dependent dioxygenases located in the lumen of the endoplasmic reticulum. Human CP4Hs are validated targets for treatment of both fibrotic diseases and metastatic breast cancer. Herein, we report on 2,2′-bipyridinedicarboxylates as inhibitors of a human CP4H. Although most 2,2′-bipyridinedicarboxylates are capable of inhibition via iron sequestration, the 4,5′- and 5,5′-dicarboxylates were found to be potent competitive inhibitors of CP4H, and the 5,5′-dicarboxylate was selective in its inhibitory activity. Our findings clarify a strategy for developing CP4H inhibitors of clinical utility.