Category: 17281-59-3

Midya, Siba Prasad published the artcileSynthesis of fused cyanopyrroles and spirocyclopropanes via addition of N-ylides to chalconimines, Computed Properties of 17281-59-3, the publication is Organic & Biomolecular Chemistry (2017), 15(17), 3616-3627, database is CAplus and MEDLINE.

Addition of N-ylides derived from DABCO to chalconimines takes place through a Michael addition-cyclization pathway to afford fused cyanopyrroles I (R = C₆H₅, 4-CH₃OC₆H₄, 4-FC₆H₄, 4-H₃CC₆H₄, 1,3-benzodioxol-5-yl) and/or spirocyclopropanes II (R = C₆H₅, 4-BrC₆H₄, 3-CH₃OC₆H₄, etc.; n = 1, 2, 3). The product profile depends heavily on the nature of chalconimines. While 6-membered cyclic chalconimines provide a mixture of pyrrole and spirocyclopropane, 5-membered chalconimines furnish exclusively spirocyclopropane. Cyclopropane was the only product in the case of a representative open chain chalconimine as well. On the other hand, chalcones provide only spirocyclopropanes which is in contrast to the previously reported reactivity of enones. The complementary nature of the reactivity of the tetralone derived chalcone and its corresponding imine in providing spirocyclopropane and pyrrole, resp., has also been demonstrated.

Organic & Biomolecular Chemistry 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, Computed Properties of 17281-59-3.

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

Moise, Iuliana-Monica published the artcileSwitching the reactivity of cyanomethylpyridinium salts in the 1,3-cycloaddition conditions with alkyl propiolates to cyanoindolizines or cyanoazaindolizinyl-indolizines, Related Products of pyridine-derivatives, the publication is Tetrahedron (2020), 76(41), 131502, database is CAplus.

A particular reactivity of 1-cyanomethylpyridinium salts was revealed in the [3 + 2] cycloaddition conditions with alkyl propiolates. Cyanoindolizines I [R = H, 7-Me, 7-OMe, etc.] were obtained in reactions carried out at room temperature while refluxing in CH₃CN provided unexpected Et or Me 3-(3-cyanoimidazo[1,2-a]pyridin-2-yl)indolizine-1-carboxylates II. The structure of the new 2:1 azaindolizine-indolizine adducts was secured by X-ray anal. Methodol. efforts had enabled the adjustment of the reactivity towards the formation of 3-cyanoindolizines I or cyanoazaindolizine-indolizines II. A mechanism for the formation of azaindolizine-indolizines was proposed.

Tetrahedron 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, Related Products of pyridine-derivatives.

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

Tominaga, Yoshinori published the artcileA new synthesis of 3,4-diaminothiophenes, Category: pyridine-derivatives, the publication is Heterocycles (1977), 6(11), 1871-6, database is CAplus.

Thiophenediamines I (R = CN, CONH₂, CO₂Et, Bz) were prepared by treating R¹CH₂CNCl^– (R¹ = pyridinio) with CS₂-NaOH, treating R¹C(CN):C(SNa)S^– with R²CH₂R (R² = Cl, Br), cyclizing R¹C(CN):C(S^–)SCH₂R with NEt₃, methylating ylides II (R³ = S^–), treating II (R³ = SMe) with MeNH₂-HCl and neutralizing. I condensed with R⁴COCOR⁴ (R⁴ = H, Me, Ph) to give the thienopyrazines III.

Heterocycles 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 C10H15NO, Category: pyridine-derivatives.

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

Tominaga, Yoshinori published the artcileSynthesis and reaction of 3,4-diaminothiophenes, Synthetic Route of 17281-59-3, the publication is Yakugaku Zasshi (1979), 99(11), 1081-90, database is CAplus.

Addition of pyridinium chloride I and CS₂ gave Ia, which was alkylated by XCH₂Y (X = Cl, Br; Y = CN, CO₂Et, Bz, CONH₂), cyclized, and iodomethylated to give II (R¹ = CN, CO₂Et, Bz, CONH₂; R² = pyridinio iodide). Cleavage of II iodide by addition of MeNH₂ followed by cyclization, acid hydrolysis, and neutralization gave II (R¹ = CN, CO₂Et, Bz, CONH₂; R² = NH₂). Also prepared were thieno[3,2-d]pyrimidinones III (R³ = Me, Ph; R⁴ = NH₂, NHBz, pyridinio chloride) and the thieno[3′,4′:4,5]imidazo[1,2-a]pyridine IV.

Yakugaku Zasshi 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 C12H9N3O4, Synthetic Route of 17281-59-3.

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

Storozhenko, Olga A. published the artcileMn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines, Recommanded Product: 1-(Cyanomethyl)pyridin-1-ium chloride, the publication is Beilstein Journal of Organic Chemistry (2018), 3078-3087, database is CAplus and MEDLINE.

The sequential three-component reaction between o-hydroxybenzaldehydes, N-(cyanomethyl)pyridinium salts and a nucleophile towards substituted chromenoimidazopyridines under oxidative conditions has been developed. The employment of Mn(OAc)₃·2H₂O or KMnO₄ as stoichiometric oxidants allowed the use of a wide range of nucleophiles, such as nitromethane, (aza)indoles, pyrroles, phenols, pyrazole, indazole and di-Et malonate. The formation of the target compounds presumably proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence.

Beilstein Journal of Organic Chemistry 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 C26H41N5O7S, Recommanded Product: 1-(Cyanomethyl)pyridin-1-ium chloride.

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

Sokolova, Ekaterina A. published the artcileHighly Fluorescent Pyrido[2,3-b]indolizine-10-Carbonitriles through Pseudo Three-Component Reactions of N-(Cyanomethyl)pyridinium Salts, Related Products of pyridine-derivatives, the publication is European Journal of Organic Chemistry (2019), 2019(40), 6770-6775, database is CAplus.

An interaction of N-(cyanomethyl)pyridinium salts with vinamidinium perchlorates or enaminones proceeds as a pseudo-three component process and results in the formation of 3- or 2-substituted pyrido[2,3-b]indolizine-10-carbonitriles, resp. Optical properties of these compounds have been evaluated, revealing effective green light emission with fluorescence quantum yields of up to 0.81.

European Journal of Organic Chemistry 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 C6H6N2O, Related Products of pyridine-derivatives.

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

Proenca, M. Fernanda published the artcileOne-pot approach to the synthesis of novel 12H-chromeno[2′,3′:4,5]imidazo[1,2-a]pyridines in aqueous media, HPLC of Formula: 17281-59-3, the publication is Tetrahedron (2010), 66(25), 4542-4550, database is CAplus.

The chromeno-imidazo[1,2-a]pyridine scaffold was generated in a one pot condensation/cyclization reaction involving a salicylaldehyde and 1-(cyanomethyl)pyridinium chloride in aqueous sodium carbonate solution These novel compounds, e.g., I, were isolated in 47-71% yield. The reaction pathway was followed by ¹H NMR spectroscopy allowing a clear understanding of the side reactions involved in the process. Different mono-substituted pyridinium chlorides were synthesized and reacted with mono-substituted salicylaldehydes and a detailed discussion of the scope of the synthetic method is also presented.

Tetrahedron 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, HPLC of Formula: 17281-59-3.

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

Proenca, Fernanda published the artcileA one-pot synthesis of substituted pyrido[2,3-b]indolizines, HPLC of Formula: 17281-59-3, the publication is Tetrahedron (2011), 67(6), 1071-1075, database is CAplus.

An efficient and novel approach to the synthesis of substituted pyrido[2,3-b]indolizine-10-carbonitriles (I; R¹, R² = Me, aryl) was developed. These structures are practically unavailable through previously described methods. The cascade transformation involves the reaction of α,β-unsaturated carbonyl compounds with a stable dimer prepared from 1-(cyanomethyl)pyridinium chloride. The reaction was performed under reflux conditions in ethanol/water and in the presence of sodium acetate. This procedure represents a eco-friendly regioselective approach to the pyrido[2,3-b]indolizine core structure.

Tetrahedron 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, HPLC of Formula: 17281-59-3.

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

Lima, Cristovao F. published the artcileNovel structurally similar chromene derivatives with opposing effects on p53 and apoptosis mechanisms in colorectal HCT116 cancer cells, COA of Formula: C7H7ClN2, the publication is European Journal of Pharmaceutical Sciences (2015), 34-45, database is CAplus and MEDLINE.

In the present work, novel chromene derivatives fused with the imidazo[1,2-a]pyridine nucleus were tested for their anticancer potential in the human colorectal cancer HCT116 cells. Compounds 2a and 2c showed significant growth inhibitory activity with GI50 of 15 μM and 11 μM, resp. Compound 2c, the most potent, has a carbamate group in position 8 of the pyridine ring, and showed significant cell cycle arrest and induction of cell death by apoptosis, even at 5 μM. Besides different potencies, chromene analogs 2a and 2c showed different mechanisms of action. Whereas the carbamate-free chromene 2a induced cell cycle arrest at G1/G0 phase, compound 2c showed to arrest cell cycle at both S and G2 phases. Chromene derivative 2a at concentrations higher than its GI50 remarkably induced caspases-dependent apoptosis in a p53-independent manner. On the other hand, compound 2c increased significantly p53 levels and induced apoptosis in a p53- and caspases-dependent manner, even at concentrations lower than its GI50. Both compounds increased the Bax/Bcl-2 ratio, induced mitochondria depolarization and activated MAP kinases. In conclusion, two novel and structurally similar chromene derivatives showed cytotoxicity to HCT16 cells through opposing effects on p53 levels and apoptosis mechanisms, which may be relevant for further development of drugs acting on distinct mol. targets useful in the treatment of cancers with different genetic profiles and for personalized medicine.

European Journal of Pharmaceutical Sciences 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, COA of Formula: C7H7ClN2.

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