Month: December 2022

Leowanawat, Pawaret published the artcileZero-Valent Metals Accelerate the Neopentylglycolborylation of Aryl Halides Catalyzed by NiCl₂-Based Mixed-Ligand Systems, Application In Synthesis of 214360-44-8, the publication is Journal of Organic Chemistry (2010), 75(22), 7822-7828, database is CAplus and MEDLINE.

The highly active mixed-ligand catalytic system NiCl₂(dppp)/dppf combined with the reducing effect of zerovalent Zn and of other metals was used to demonstrate a method for the dramatic acceleration of the rate and for the enhancement of the yield of Ni-catalyzed neopentylglycolborylation of aryl halides. A diversity of electron-rich and electron-deficient aryl iodides, bromides, and chlorides were efficiently neopentylglycolborylated, typically in 1 h or less. This acceleration is particularly remarkable for the generally less reactive aryl bromides and chlorides and for all ortho-substituted aryl halides. By accelerating the rate of borylation and reducing its reaction time to complete conversion, pathways leading to protodeborylated or hydrodehalogenated side products have a reduced impact on the outcome of the overall reaction. Although Zn powder was the reducing agent of choice, compatibility of this technique with more readily recoverable Zn chips, as well as other metals such as Mn, Mg, Fe, Al, and Ca, demonstrated the broad scope of this synthetic method.

Journal of Organic Chemistry published new progress about 214360-44-8. 214360-44-8 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Boronic acid and ester,Benzene,Boronic Acids,Boronic acid and ester, name is 4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile, and the molecular formula is C12H14BNO2, Application In Synthesis of 214360-44-8.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Quan, Xue-Jing published the artcilep-Toluenesulfonic Acid Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN₃ for Synthesis of 4-Aryl-NH-1,2,3-triazoles [Erratum to document cited in CA161:682131], Name: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2015), 17(2), 393, database is CAplus and MEDLINE.

On page 5730, structure 4a in Scheme 2 was published incorrectly, and subsequent text corresponding to this Structure is also incorrect; the correct structure, name, and text are given.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Name: (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Quan, Xue-Jing published the artcilep-Toluenesulfonic Acid Mediated 1,3-Dipolar Cycloaddition of Nitroolefins with NaN₃ for Synthesis of 4-Aryl-NH-1,2,3-triazoles, Safety of (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic Letters (2014), 16(21), 5728-5731, database is CAplus and MEDLINE.

A p-TsOH-mediated 1,3-dipolar cycloaddition of nitroolefins and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed. p-TsOH was discovered as a vital additive in this type of 1,3-dipolar cycloaddition This novel cycloaddition reaction is a good method for the rapid synthesis of valuable 4-aryl-NH-1,2,3-triazoles in high yields.

Organic Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, Safety of (E)-4-(2-Nitrovinyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Benmohammed, Abdelmadjid published the artcileSynthesis and antimicrobial activities of new thiosemicarbazones and thiazolidinones in indole series, Quality Control of 612-13-5, the publication is Monatshefte fuer Chemie (2021), 152(8), 977-986, database is CAplus.

New thiosemicarbazones I [R¹ = H, 3-Cl, 4-F, etc.; R² = H, OMe] were synthesized via condensation of N-benzylindole-3-carboxaldehydes with N⁴-substituted thiosemicarbazides in excellent yield. These thiosemicarbazones I were reacted with Et bromoacetate to produce original heterocyclic-substituted indole derivatives possessing a 4-oxo-thiazolidine group II. Anal. IR and NMR spectra and elemental anal. were performed to reveal their structures. The antimicrobial activity of all synthesized compounds was evaluated for antibacterial activity in vitro against Gram-pos. and Gram-neg. bacteria. Antibacterial screening data showed that two compounds I and II demonstrated activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. These preliminary results indicated that newly synthesized compounds such as I [R¹ = 3-Cl, R² = OMe] and II [R¹ = H, R² = H] showed a promising antibacterial potency.

Monatshefte fuer Chemie published new progress about 612-13-5. 612-13-5 belongs to nitriles-buliding-blocks, auxiliary class Organic Pigment, name is 2-(Chloromethyl)benzonitrile, and the molecular formula is C8H6ClN, Quality Control of 612-13-5.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sochacka-Cwikla, Aleksandra published the artcileSynthesis and biological activity of new 7-amino-oxazolo[5,4-d]pyrimidine derivatives, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate, the publication is Molecules (2020), 25(15), 3558, database is CAplus and MEDLINE.

The synthesis of a series of novel 7-aminooxazolo[5,4-d]pyrimidines I (R = Me, Et, cyclohexyl, etc.), transformations during their synthesis and their physicochem. characteristics have been described. Complete detailed spectral anal. of the intermediates, the N’-cyanooxazolylacetamidine byproducts and final compounds I was carried out using MS, IR, 1D and 2D NMR spectroscopy. Theor. research was carried out to explain the privileged formation of 7-aminooxazolo[5,4-d]pyrimidines in relation to the possibility of their isomer formation and the related thermodn. aspects. Addnl., the single-crystal X-ray diffraction anal. for compound I [R = 2-(morpholin-4-yl)ethyl] was reported. Ten 7-aminooxazolo[5,4-d]pyrimidines I were biol. tested in vitro to preliminarily evaluate their immunol., antiviral and anticancer activity. Compounds I [R = n-pentyl, 3-(N,N-dimethylamino)propyl] showed the best immunoregulatory profile. These compounds displayed low-toxicity and strongly inhibited phytohemagglutinin A-induced proliferation of human peripheral blood lymphocytes and lipopolysaccharide-induced proliferation of mouse splenocytes. Compound I [R = 3-(N,N-dimethylamino)propyl] caused also a moderate suppression of tumor necrosis factor α (TNF-α) production in a human whole blood culture. Of note, the compounds also inhibited the growth of selected tumor cell lines and inhibited replication of human herpes virus type-1 (HHV-1) virus in A-549 cell line. Mol. investigations showed that the compounds exerted differential changes in expression of signaling proteins in Jurkat and WEHI-231 cell lines. The activity of the compound I (R = n-pentyl) is likely associated with elicitation of cell signaling pathways leading to cell apoptosis.

Molecules published new progress about 5098-14-6. 5098-14-6 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Salt,Sulfonic acid,Amine,Benzene, name is 2-Aminomalononitrile 4-methylbenzenesulfonate, and the molecular formula is C5H8N2O, Recommanded Product: 2-Aminomalononitrile 4-methylbenzenesulfonate.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Maripally, Narsimulu published the artcileDMAP catalyzed addition-cyclization reaction of 2-hydroxyphenyl-para-quinone methide with nitroalkenes: facile entry into highly substituted chromane derivatives, SDS of cas: 5153-73-1, the publication is Tetrahedron Letters (2020), 61(9), 151554, database is CAplus.

The base catalyzed reaction of 2-hydroxyphenyl-para-quinone methide (p-QM) with nitroalkenes was reported. The DMAP-catalyzed reaction afforded substituted chromane derivatives I [R = H, 7-Me, 6-MeO, 6-F, 6-Cl, 6-Br; R¹ = i-Bu, Ph, 2-thienyl, etc.; stereo = R or S] in excellent yields with moderate diastereoselectivity. The conversion of the initial products to other useful structures was also achieved.

Tetrahedron Letters published new progress about 5153-73-1. 5153-73-1 belongs to nitriles-buliding-blocks, auxiliary class Nitrile,Alkenyl,Nitro Compound,Benzene, name is (E)-4-(2-Nitrovinyl)benzonitrile, and the molecular formula is C9H6N2O2, SDS of cas: 5153-73-1.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Gull, Yasmeen published the artcileSynthesis of N-(6-arylbenzo[d]thiazole-2-acetamide) derivatives and their biological activities: an experimental and computational approach, Related Products of nitriles-buliding-blocks, the publication is Molecules (2016), 21(3), 66/1-66/17, database is CAplus and MEDLINE.

Synthesis of N-(6-arylbenzo[d]thiazol-2-yl)acetamides I [Ar = Ph, 4-MeC₆H₄, 3-Cl-4-FC₆H₃, etc.] by C-C coupling methodol. in the presence of Pd(0) using various aryl boronic pinacol ester/acids was reported. The newly synthesized compounds I were evaluated for various biol. activities like antioxidant, hemolytic, antibacterial and urease inhibition. In bioassays these I compounds were found to have moderate to good activities. Among the tested biol. activities screened these I compounds displayed the most significant activity for urease inhibition. In urease inhibition, all compounds were found more active than the standard used. The compound I [Ar = Ph, 4-MeC₆H₄] was found to be the most active. To understand this urease inhibition, mol. docking studies were performed. The in silico studies showed that these acetamide derivatives bind to the non-metallic active site of the urease enzyme. Structure-activity studies revealed that H-bonding of compounds with the enzyme was important for its inhibition.

Molecules published new progress about 479411-95-5. 479411-95-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzonitrile, and the molecular formula is C14H15BF3NO2, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Ali, Shaukat published the artcileDesign and synthesis of arylthiophene-2-carbaldehydes via Suzuki-Miyaura reactions and their biological evaluation, Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzonitrile, the publication is Molecules (2013), 18(12), 14711-14725, database is CAplus and MEDLINE.

A series of 4-arylthiophene-2-carbaldehydes I [R = Ph, 5-Me-2-thienyl, 3,5-(F₃C)₂C₆H₃, etc.] were synthesized in moderate to excellent yields via Suzuki-Miyaura cross-coupling with different arylboronic pinacol esters/acids. The synthesized products were screened for their antibacterial, hemolytic, antiurease, nitric oxide (NO) scavenging capabilities and almost all products exhibited good activities. Compound I [R = 3-CN-5-F₃C-C₆H₃] revealed excellent antibacterial activity and was also found to be the best NO scavenger with an IC₅₀ value of 45.6 μg/mL. Moreover, compound I [R = 4-F-3-Cl-C₆H₃] exhibited a superior hemolytic action and an outstanding urease inhibition with an IC₅₀ value of 27.1 μg/mL.

Molecules published new progress about 479411-95-5. 479411-95-5 belongs to nitriles-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Nitrile,Boronic acid and ester,Benzene,Boronate Esters,Boronic Acids,Boronic acid and ester, name is 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzonitrile, and the molecular formula is C14H15BF3NO2, Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-5-(trifluoromethyl)benzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Franke, Jenna M. published the artcileBODIPY Fluorophores for Membrane Potential Imaging, Safety of 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, the publication is Journal of the American Chemical Society (2019), 141(32), 12824-12831, database is CAplus and MEDLINE.

Fluorophores based on the BODIPY scaffold are prized for their tunable excitation and emission profiles, mild syntheses, and biol. compatibility. Improving the water-solubility of BODIPY dyes remains an outstanding challenge. The development of water-soluble BODIPY dyes usually involves direct modification of the BODIPY fluorophore core with ionizable groups or substitution at the boron center. While these strategies are effective for the generation of water-soluble fluorophores, they are challenging to implement when developing BODIPY-based indicators: direct modification of BODIPY core can disrupt the electronics of the dye, complicating the design of functional indicators; and substitution at the boron center often renders the resultant BODIPY incompatible with the chem. transformations required to generate fluorescent sensors. In this study, we show that BODIPYs bearing a sulfonated aromatic group at the meso position provide a general solution for water-soluble BODIPYs. We outline the route to a suite of 5 new sulfonated BODIPYs with 2,6-disubstitution patterns spanning a range of electron-donating and -withdrawing propensities. To highlight the utility of these new, sulfonated BODIPYs, we further functionalize them to access 13 new, BODIPY-based, voltage-sensitive fluorophores (VF). The most sensitive of these BODIPY VF dyes displays a 48% ΔF/F per 100 mV in mammalian cells. Two addnl. BODIPY VFs show good voltage sensitivity (≥24% ΔF/F) and excellent brightness in cells. These compounds can report on action potential dynamics in both mammalian neurons and human stem cell-derived cardiomyocytes. Accessing a range of substituents in the context of a water-soluble BODIPY fluorophore provides opportunities to tune the electronic properties of water-soluble BODIPY dyes for functional indicators.

Journal of the American Chemical Society published new progress about 26187-28-0. 26187-28-0 belongs to nitriles-buliding-blocks, auxiliary class Pyrrole,Nitrile, name is 2,4-Dimethyl-1H-pyrrole-3-carbonitrile, and the molecular formula is C7H8N2, Safety of 2,4-Dimethyl-1H-pyrrole-3-carbonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wang, Chengpeng published the artcileDirect β-Alkenylation of Ketones via Pd-Catalyzed Redox Cascade, Computed Properties of 68569-14-2, the publication is Organic Letters (2019), 21(9), 3377-3381, database is CAplus and MEDLINE.

A direct β-alkenylation of simple ketones with alkenyl bromides is reported via a Pd-catalyzed redox cascade strategy. The reaction is redox neutral and directing-group-free, in the absence of strong acids or bases. Both cyclic and linear ketones are suitable substrates, and various alkenyl bromides can be coupled. The resulting β-alkenyl ketones are readily derivatized through diverse alkene functionalization.

Organic Letters published new progress about 68569-14-2. 68569-14-2 belongs to nitriles-buliding-blocks, auxiliary class Palladium, name is Tetrakis(acetonitrile)palladium(II) Ditriflate, and the molecular formula is C5H10Cl3O3P, Computed Properties of 68569-14-2.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts