Tag: M.W=150-200

Xing, Kai published the artcileA self-calibrating dual responsive platform for the sensitive detection of sulfite and sulfonic derivatives based on a robust Hf(IV) metal-organic framework, Computed Properties of 636-73-7, the publication is Chemical Communications (Cambridge, United Kingdom) (2020), 56(4), 631-634, database is CAplus and MEDLINE.

A robust hafnium-based metal organic framework, Hf-PBTA, with sensitive and self-calibrating dual-emissive fluorescence response towards sulfite and sulfonic derivatives, including antibiotic sulfamethazine, has been developed, which shows fast detection of sulfite ions at a concentration as low as 76 ppb. The opposite response tendency from two radiative pathways towards aromatic sulfonic mols. and sulfite anions stems from the synergistic effect of the pyridine protonation effect, π-π stacking interaction and intramol. twist motion.

Chemical Communications (Cambridge, United Kingdom) published new progress about 636-73-7. 636-73-7 belongs to pyridine-derivatives, auxiliary class Pyridine,Sulfonic acid, name is Pyridine-3-sulfonic acid, and the molecular formula is C15H14O3, Computed Properties of 636-73-7.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Liu, Yanjie published the artcileFeCl₂ Catalyzed Three-Component Reactions of Phospholes, Pyrrolidine, and Ketones (Aldehydes): Chemoselective Synthesis of 1-Phosphafulvenes, Quality Control of 91-02-1, the publication is Organic Letters (2021), 23(8), 2943-2947, database is CAplus and MEDLINE.

The authors have developed an unprecedented approach for the synthesis of transient 1-phosphafulvenes through three component reactions of phospholes. The generation of 1-phosphafulvenes was demonstrated by in situ [6 + 4] cycloaddition with 2H-phospholes and [6 + 6] self-dimerization. The [6 + 4] and [6 + 6] reaction pathway could be modulated by the starting ketones and aldehydes. The construction of 1-phosphafulvenes is illustrated by a proposed mechanism combining nucleophilic addition of phospholide to the iminium or isomerized azomethine ylide and a [1,5]-shift of phosphole.

Organic Letters published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C12H9NO, Quality Control of 91-02-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Dai, Jian-Jun published the artcileCopper-Promoted Sandmeyer Trifluoromethylation Reaction, HPLC of Formula: 39856-58-1, the publication is Journal of the American Chemical Society (2013), 135(23), 8436-8439, database is CAplus and MEDLINE.

A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.

Journal of the American Chemical Society published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, HPLC of Formula: 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Zhao, Jing published the artcileA liquid chromatography-mass spectrometry workflow for in-depth quantitation of fatty acid double bond location isomers, COA of Formula: C12H9NO, the publication is Journal of Lipid Research (2021), 100110, database is CAplus and MEDLINE.

Tracing compositional changes of fatty acids (FAs) is frequently used as a means of monitoring metabolic alterations in perturbed biol. states. Given that more than half of FAs in the mammalian lipidome are unsaturated, quantitation of FAs at a carbon-carbon double bond (C=C) location level is necessary. The use of 2-acetylpiridine (2-acpy) as the charge-tagging PB reagent led to a limit of identification in the subnanomolar range for mono- and polyunsaturated as well as conjugated FAs. Conjugated free FAs of low abundance such as FA 18:2 (n-7, n-9) and FA 18:2 (n-6, n-8) were quantified at concentrations of 0.61 ± 0.05 and 0.05 ± 0.01 mg per 100 g in yak milk powder, resp. This workflow also enabled deep profiling of eight saturated and 37 unsaturated total FAs across a span of four orders of magnitude in concentration, including ten groups of C=C location isomers in pooled human plasma. A pilot survey on total FAs in plasma from patients with type 2 diabetes revealed that the relative compositions of FA 16:1 (n-10) and FA 18:1 (n-10) were significantly elevated compared with that of normal controls. In this work, we have developed a workflow for global quantitation of FAs, including C=C location isomers, via charge-tagging Paterno-Buchi (PB) derivatization and liquid chromatog.-tandem mass spectrometry (LC-MS/MS).

Journal of Lipid Research published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C21H24O8, COA of Formula: C12H9NO.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Wang, Peng published the artcileLigand-Promoted Meta-C-H Arylation of Anilines, Phenols, and Heterocycles, Quality Control of 90778-25-9, the publication is Journal of the American Chemical Society (2016), 138(29), 9269-9276, database is CAplus and MEDLINE.

The authors report the development of a versatile 3-acetylamino-2-hydroxypyridine class of ligands that promote meta-C-H arylation of anilines, heterocyclic aromatic amines, phenols, and 2-benzyl heterocycles using norbornene as a transient mediator. More than 120 examples are presented, demonstrating this ligand scaffold enables a wide substrate and coupling partner scope. Meta-C-H arylation with heterocyclic aryl iodides as coupling partners is also realized for the first time using this ligand. The utility for this transformation for drug discovery is showcased by allowing the meta-C-H arylation of a lenalidomide derivative The first steps toward a silver-free protocol for this reaction are also demonstrated.

Journal of the American Chemical Society published new progress about 90778-25-9. 90778-25-9 belongs to pyridine-derivatives, auxiliary class Trifluoromethyl,Pyridine,Fluoride,Amine,Alcohol, name is 3-Amino-5-(trifluoromethyl)pyridin-2-ol, and the molecular formula is C17H14N2O2, Quality Control of 90778-25-9.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Cook, A. H. published the artcilePreparation of diarylmaleonitriles, Application In Synthesis of 17281-59-3, the publication is Journal of the Chemical Society (1941), 502-6, database is CAplus.

cf. C. and Linstead, C. A. 31, 6237.5. 2,1-HOC₁₀H₆CHO (29 g.) and 15 g. of amalgamated Zn in 300 cc. moist ether, boiled overnight and the product treated with HCl, give 310 mg. of 1,2-bis(2-hydroxy-1-naphthyl)ethylene, m. 252°; di-Me ether (I), m. 222°; both give deep red solutions in concentrated H₂SO₄; light absorption in petr. ether:maximum 3420, 2910 A.; inflection, 2800 A.; E^1%_1cm. 185, 217, 303, resp. The other products are (2,1-HOC₁₀H₆)₂CH₂ and 24 g. of 2,1-HOC₁₀H₆CH₂OH (II). II could not be converted to the bromide or iodide. Addition of 25 g. of 2-C₁₀H₇OMe in 250 cc. AcOH to a solution of 10 g. (HCHO)₃ in 150 cc. AcOH (which had been treated with dry HCl until a clear solution results) and treatment with HCl give, after standing overnight, 21 g. of 2-methoxy-1-chloromethylnaphthalene (III), decomposes at 120° (evolution of HCl); hydrolysis with aqueous NaHCO₃ in Me₂CO gives 2,1-MeOC₁₀H₆CH₂OH. Warming III with dilute EtOH-alkali at 40° for several hrs. gives (2-methoxy-1-naphthyl)-carbinyl Et ether, b₁₂ 173-5°. III (18 g.) in 600 cc. Me₂CO with 12 g. KCN in 300 cc. H₂O at 30-5° gives 16 g. of 2-methoxy-1-naphthaleneacetonitrile (IV), m. 111°. III with AgNO₃ in Me₂CO-EtOH at 30° for 24 h. gives the β-form of I, m. 145°; light absorption in petr. ether: maximum 3380, 2960 A.; inflection 2830 A.; E^1%_1cm. 180, 270, 300, resp. Both forms give orange colors with concentrated H₂SO₄; both are unsaturated toward C(NO₂)₄ but neither is appreciably changed by exposure to UV light in C₆H₆ solution The 2 ethers are probably cis and trans isomers with relative stabilities not infrequently encountered among isomeric stilbenes. IV in CHCl₃ containing CaCO₃ gives a Br derivative, m. 145-6°; this did not react with C₅H₅N. IV does not yield the desired diarylmaleonitrile with Br or I and bases under the most diverse conditions. 2,1-MeC₁₀H₆CH₂Cl (V) and KCN in 85% EtOH give 2-methyl-1-naphthaleneacetonitrile, m. 78°; when more H₂O is used in the reaction, the product is (2-methyl-1-naphthyl)carbinol, m. 137-8°; this loses H₂O at 100° in vacuo but could not be reconverted to V with EtOHHCl at room temperature 2,1-MeOC₁₀H₆CHO yields a cyanohydrin (VI), m. 111°; with SOCl₂ in C₆H₆ at room temperature for 30 min. VI gives bis[(2-methoxy-1-naphthyl)cyanomethyl] ether (VII), m. 121°. When VI or VII is boiled for 20 min. with an excess of SOCl₂, there results 50% of α-chloro-2-methoxy-1-naphthaleneacetonitrile, m. 130°; solution in warm C₅H₅N gives 1-[(2-methoxy-1-naphthyl)-cyanomethyl]pyridinium chloride (VIII), m. 165° (slight decomposition); aqueous Na₂CO₃ gives an orange precipitate of 1-[(2-methoxy-1-naphthyl) cyanomethyl] pyridinium enimine-betaine, m. 150° (decomposition); heating at 200°/0.001 mm. liberates C₅H₅N and gives IV and bis(2-methoxy-1-naphthyl)maleonitrile (IX); passage through Al₂O₃ gives about 5% of the α form, pale yellow, m. 255°, and 5% of the β form, pale yellow, m. 290°; the yield of IX is much smaller on heating VIII. On heating IX with Cu or Cu salts produces results which give intense green colors in C₅H₅N with strong absorption of light at 6250 A. ClCH₂CN and C₅H₅N give the very deliquescent (cyanomethyl)pyridinium chloride (X), m. 178°; aqueous KOH or K₂CO₃ gave the yellow betaine, which easily resinified and could not be crystallized X and Bz₂O in CHCl₃, shaken with aqueous K₂CO₃, give the light yellow Bz derivative of the betaine, m. 145°, identical with Kröhnke’s (ω-cyanophenacyl)pyridinium benzoate (C. A. 33, 2522.9). ClCH₂CONH₂ gives acetamidopyridinium chloride, m. 202-3°; it gives no betaine with alkali. PhClCHCN in C₅H₅N gives (α-cyanobenzyl)pyridinium chloride (XI), m. 159°. The red enimine-betaine, sublimed at 120° in vacuo, gives about 50% of diphenylmaleonitrile; distillation of XI in vacuo gives about 10%. It appears, therefore, that dimerization proceeds only with arylhaloacetonitriles. PhCH₂CH(OH)CN and PCl₅ in C₆H₆, warmed until solution results, give 62% of α-chloro-β-phenylpropionitrile, b₁₃ 128-30°; boiling with quinoline gives PhCH:CHCN in practically quant. yield. PhCH:CH(OH)CN and SOCl₂ give a product b₁₅ 130-40°; this is mainly α-chloro-γ-phenylvinylacetonitrile, but it could not be obtained pure because it continually deposits a compound m. 114°, probably 2,5-diphenyldihydroterephthalonitrile; it yielded no porphyrazine pigment. p-MeOC₆H₄CH(OH)CN (12 g.) and 10% excess of SOCl₂ give 7 g. of (p-methoxyphenyl)-chloroacetonitrile (XII), b₁₃ 153-5°; sublimation of the residue in the distillation flask in vacuo gives bis(p-methoxyphenyl)maleonitrile, m. 186-7°; this also is formed by the direct action of C₅H₅N on XII. A C₅H₅N solution of the melt obtained on heating with Fe at 300° is an intense green color and showed characteristic porphyrazine spectral absorption bands (6320, 5800 A.).

Journal of the Chemical Society published new progress about 17281-59-3. 17281-59-3 belongs to pyridine-derivatives, auxiliary class Pyridine,Nitrile,Salt, name is 1-(Cyanomethyl)pyridin-1-ium chloride, and the molecular formula is C7H7ClN2, Application In Synthesis of 17281-59-3.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Cory, Joseph G. published the artcileSubstituted 2-acylpyridine-α-(N)-hetarylhydrazones as inhibitors of ribonucleotide reductase activity and L1210 cell growth, Quality Control of 2215-33-0, the publication is Anticancer Research (1994), 14(3A), 875-9, database is CAplus and MEDLINE.

A series of substituted 2-acylpyridine-α-(N)-hetarylhydrazones was prepared and studied for their effects on mammalian ribonucleotide reductase activity using a highly purified enzyme preparation from Ehrlich tumor cells and on mouse leukemia L1210 cell growth in culture. Pyridine-2-aldehyde-2-pyridylhydrazone (PH 22), ethyl-2-pyridylketone-1-phthalazinylhydrazone (PH 22-25) and pyridine-2-aldehyde-2′-quinolylhydrazone (PQ 22) inhibited purified ribonucleotide reductase activity and inhibited L1210 cell growth in culture. PH 22-25 inhibited [³H]thymidine incorporation into DNA and inhibited ribonucleotide reductase activity in situ (as measured by [¹⁴C]cytidine metabolism) and as a result inhibited DNA synthesis. There was no effect on RNA synthesis. These data indicate that these substituted hydrazones are potent inhibitors of tumor cell growth through the inhibition of ribonucleotide reductase.

Anticancer Research published new progress about 2215-33-0. 2215-33-0 belongs to pyridine-derivatives, auxiliary class Pyridine,Amine, name is 2-((2-(Pyridin-2-yl)hydrazono)methyl)pyridine, and the molecular formula is C11H10N4, Quality Control of 2215-33-0.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Zhang, Jin published the artcileSelective Oxidation of Alkylarenes to the Aromatic Ketones or Benzaldehydes with Water, Recommanded Product: Phenyl(pyridin-2-yl)methanone, the publication is Organic Letters (2022), 24(5), 1152-1157, database is CAplus and MEDLINE.

Here a palladium-catalyzed oxidation method for converting alkylarenes into the aromatic ketones or benzaldehydes ArC(O)R¹ [Ar = Ph, 4-MeC₆H₄, 4-HOC₆H₄, etc.; R¹ = H, Ph, 4-ClC₆H₄, etc.] with water as the only oxygen donor was reported. This C-H bond oxidation functionalization did not require other oxidants and hydrogen acceptors, and H₂ was the only byproduct. The oxygen atom introduced into the products was confirmed to be from water by the MS anal. on the product of the ¹⁸O-labeled water reaction.

Organic Letters published new progress about 91-02-1. 91-02-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Benzene,Ketone, name is Phenyl(pyridin-2-yl)methanone, and the molecular formula is C8H6ClF3, Recommanded Product: Phenyl(pyridin-2-yl)methanone.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Deau, Emmanuel published the artcileMicrowave-assisted synthesis of novel N-(4-phenylthiazol-2-yl)-benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides inspired by marine topsentines and nortopsentines, Synthetic Route of 39856-58-1, the publication is Tetrahedron (2014), 70(35), 5532-5540, database is CAplus.

We report the synthesis of novel N-(4-phenylthiazol-2-yl)-substituted benzo[d]thiazole-, thiazolo[4,5-b]pyridine-, thiazolo[5,4-b]pyridine- and benzo[d]oxazole-2-carboximidamides, which were inspired by marine topsentines and nortopsentines. Condensation of 4,5-dichloro-1,2,3-dithiazolium chloride (Appel salt) with various ortho-halogenated anilines, aminopyridines and aminophenols gave the corresponding aryliminodithiazoles in good to excellent yields. Copper(I)-mediated or nucleophilic-assisted cyclization of aryliminodithiazoles furnished cyano-functionalized benzo[d]thiazoles, thiazolo[4,5-b]- and thiazolo[5,4-b]-pyridines and benzo[d]oxazoles. The latter were condensed with substituted 4-phenylthiazol-2-amines to furnish twenty seven new polyaromatic carboximidamides in moderate to good yields.

Tetrahedron published new progress about 39856-58-1. 39856-58-1 belongs to pyridine-derivatives, auxiliary class Pyridine,Bromide,Amine, name is 2-Bromopyridin-3-amine, and the molecular formula is C5H5BrN2, Synthetic Route of 39856-58-1.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem

Bremner, D. H. published the artcileThe synthesis of thienopyridines from ortho-halogenated pyridine derivatives. Part 2, Safety of Ethyl 2-(2-chloropyridin-3-yl)acetate, the publication is Synthesis (1997), 949-952, database is CAplus.

Synthetic routes to 2- and 4-chloro-3-pyridylacetate, 3-bromo-4-pyridylacetate, and 3-bromo-2-pyridylacetate containing methylene groups activated by the ester functionality are reported. Reaction of these pyridines with CS₂ in the presence of NaH, followed by quenching with MeI results in the formation of the corresponding thienopyridines in moderate yields.

Synthesis published new progress about 164464-60-2. 164464-60-2 belongs to pyridine-derivatives, auxiliary class Pyridine,Chloride,Ester, name is Ethyl 2-(2-chloropyridin-3-yl)acetate, and the molecular formula is C9H10ClNO2, Safety of Ethyl 2-(2-chloropyridin-3-yl)acetate.

Referemce:
https://en.wikipedia.org/wiki/Pyridine,
Pyridine | C5H5N – PubChem