Author: Jessica.F

Zheng, Kai-Lu published the artcileAcid-Mediated Intermolecular [3 + 2] Cycloaddition toward Pyrrolo[2,1-a]isoquinolines: Total Synthesis of the Lamellarin Core and Lamellarin G Trimethyl Ether, Application In Synthesis of 5153-73-1, the publication is Organic Letters (2017), 19(9), 2262-2265, database is CAplus and MEDLINE.

A novel one-pot reaction was developed for the efficient synthesis of pyrrolo[2,1-a]isoquinolines and 1-dearyllamellarin core from (E)-(2-nitrovinyl)benzenes and azomethine ylides generated in situ. This strategy provides a concise total synthesis of the lamellarin core I and lamellarin G tri-Me ether using electrophilic substitution and palladium-catalyzed Suzuki-Miyaura cross-coupling reactions.

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 C15H24S, Application In Synthesis of 5153-73-1.

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

Hao, Feiyue published the artcileDirect dihalo-alkoxylation of nitroalkenes leading to β,β-dihalo-β-nitroethyl alkyl ethers, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile, the publication is Organic & Biomolecular Chemistry (2018), 16(15), 2768-2775, database is CAplus and MEDLINE.

A highly efficient one-pot synthesis of β,β-dihalo-β-nitroethyl alkyl ethers such as I [R = Ph, 4-MeOC₆H₄, 2-naphthyl, etc.; R¹ = Me, n-Pr, F₃CH₂C, etc.; R² = H, F, Cl, Br, I; R³ = H, Cl, Br] was achieved by the treatment of nitroalkenes with alcs. and N-halosuccinimides in the presence of sodium hydride. The notable advantages of this protocol were mainly the involvement of simple exptl. manipulations and tolerance of a wide range of functional groups. Further transformations of the obtained ethers I, such as allylation and conversion to β,β-dihalogenated vinyl ethers, were also investigated.

Organic & Biomolecular Chemistry 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, Recommanded Product: (E)-4-(2-Nitrovinyl)benzonitrile.

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

Yang, Weibo published the artcileOrchestrated Triple C-H Activation Reactions Using Two Directing Groups: Rapid Assembly of Complex Pyrazoles, Safety of Tetrakis(acetonitrile)palladium(II) Ditriflate, the publication is Angewandte Chemie, International Edition (2015), 54(8), 2501-2504, database is CAplus and MEDLINE.

A sequential triple C-H activation reaction directed by a pyrazole and an amide group leads to the well-controlled construction of sterically congested dihydrobenzo[e]indazole derivs I [R¹ = H, 4-Me, 3-Me, 3,4-diMe, 4-Ph, 4-F, etc.; R² = Me, (CH₂)₂Ph, (CH₂)₃Ph; R³ = Me, Et, iBu, cyclohexylmethyl; R²R³=(CH₂)₅; R⁴ = Me, Et]. This cascade reaction demonstrates that the often problematic competing C-H activation pathways in the presence of multiple directing groups can be harvested by design to improve step economy in synthesis. Pyrazole as a relatively weak coordinating group is shown to direct Csp³-H activation for the first time.

Angewandte Chemie, International Edition 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 C17H18N2O6, Safety of Tetrakis(acetonitrile)palladium(II) Ditriflate.

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

Han, Xiaoyu published the artcileA highly enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins mediated by a bifunctional quinine derived thiourea catalyst, COA of Formula: C9H6N2O2, the publication is Organic & Biomolecular Chemistry (2017), 15(16), 3401-3407, database is CAplus and MEDLINE.

A useful enantioselective Friedel-Crafts reaction of 3,5-dimethoxylphenol with nitroolefins catalyzed by a bifunctional quinine derived thiourea catalyst was developed. The Michael addition products could be obtained in good to high yields (68-92%) and with excellent enantioselectivities (89-98% ee). Such a reaction is exceptionally attractive in virtue of its simple protocol, ready availability of the starting materials, and practical applications of the products.

Organic & Biomolecular Chemistry 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, COA of Formula: C9H6N2O2.

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

Dou, Xiaowei published the artcileAsymmetric synthesis of 3-spirocyclopropyl-2-oxindoles via intramolecular trapping of chiral aza-ortho-xylylene, Category: nitriles-buliding-blocks, the publication is Chemical Communications (Cambridge, United Kingdom) (2013), 49(80), 9224-9226, database is CAplus and MEDLINE.

Chiral aza-ortho-xylylene intermediates were efficiently generated from 3-chloro-3-substituted oxindole precursors I (R = H, 5-Br, 6-Cl, 5-Cl) and (E)-R¹CH:CHNO₂ (R¹ = Ph, 2-BrC₆H₄, 3-BrC₆H₄, 3-ClC₆H₄, 4-ClC₆H₄, 4-FC₆H₄, 2-MeC₆H₄, 4-MeOC₆H₄, 4-NCC₆H₄, 1-naphthyl, 2-furyl, 2-thienyl, phenethyl). The process was catalyzed by chiral quinine derivative II. The first intramol. trapping of chiral aza-ortho-xylylene intermediates led to a highly asym. synthesis of 3-spirocyclopropyl-2-oxindoles III.

Chemical Communications (Cambridge, United Kingdom) 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, Category: nitriles-buliding-blocks.

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

Chen, Peiran published the artcileKinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, the publication is Tetrahedron Letters (2014), 55(14), 2290-2294, database is CAplus.

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Tetrahedron Letters published new progress about 13312-84-0. 13312-84-0 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Alcohol,Benzene Compounds, name is 2-(2-Chlorophenyl)-2-hydroxyacetonitrile, and the molecular formula is C8H6ClNO, Safety of 2-(2-Chlorophenyl)-2-hydroxyacetonitrile.

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

Zhang, Mengmeng published the artcileVisible Light Mediated C(sp³)-H Alkenylation of Cyclic Ethers Enabled by Aryl Ketone, Formula: C9H6N2O2, the publication is ChemCatChem (2019), 11(6), 1606-1609, database is CAplus.

C-H Alkenylation of cyclic ethers (THF, 1,4-dioxane) using the readily available nitroalkenes as the alkenylating reagents which gave α-alkenyl ethers Ar(CH:CH)_nR [Ar = Ph, 2-naphthyl, 2-thienyl, etc.; R = 1,2-dimethoxyethane, tetrahydrofuran-2-yl, 1,4-dioxan-2-yl] with high E-selectivity was developed. The mechanism study revealed that alkenylation proceeded through a proton coupled electron transfer (PCET) process with a de-nitration.

ChemCatChem 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 C8H16O2, Formula: C9H6N2O2.

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

Zhang, Chun-Bo published the artcileDesign and synthesis of 6-alkyloxy[1,2,4]triazolo[1,5-a]quinazoline derivatives with anticonvulsant activity, Synthetic Route of 612-13-5, the publication is Medicinal Chemistry Research (2012), 21(10), 3294-3300, database is CAplus.

6-(Benzyloxy or alkoxy)[1,2,4]triazolo[1,5-a]quinazoline derivatives were synthesized in four steps starting from 1,3-cyclohexanedione, DMF-DMA, and aminotriazole followed by bromination, dehydrobromination and finally reaction with benzyl or alkyl halides. The anticonvulsant activity of all the target compounds, characterized by IR, ¹H-NMR and MS, were evaluated using Maximal electroshock test. The pharmacol. results showed that some of the compounds displayed pos. anticonvulsant activity. Among them, 6-(benzyloxy)-[1,2,4]triazolo[1,5-a]quinazoline was the most active compound with an ED₅₀ value of 78.9 mg/kg and a PI value of 9.0.

Medicinal Chemistry Research 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 C22H18Cl2N2, Synthetic Route of 612-13-5.

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

Li, Guoshuai published the artcilePalladium-Catalyzed meta-Selective C-H Functionalization by Noncovalent H-Bonding Interaction, Recommanded Product: 2-Fluoro-4,5-dimethoxybenzonitrile, the publication is ACS Catalysis (2021), 11(16), 10460-10466, database is CAplus.

Herein, a palladium-catalyzed meta-selective C-H olefination of aromatic carbonyl compounds such as acetophenone, benzaldehyde, Me benzoate, N,N-diisopropylbenzamide, etc. by noncovalent hydrogen-bonding interaction was reported. N,N’-Substituted ureas RNHC(O)NHR¹ [R = cyclohexyl, 3,5-bis(trifluoromethyl)phenyl; R¹ = cyclohexyl, 2-(2-cyanophenoxy)ethyl, 2-phenoxyethyl, etc.] were engineered to serve as a H-bonding donor for binding to the substrates and, meanwhile, achieve site-selective control by the integrated directing group.

ACS Catalysis published new progress about 119396-88-2. 119396-88-2 belongs to nitriles-buliding-blocks, auxiliary class Fluoride,Nitrile,Benzene,Ether, name is 2-Fluoro-4,5-dimethoxybenzonitrile, and the molecular formula is C9H8FNO2, Recommanded Product: 2-Fluoro-4,5-dimethoxybenzonitrile.

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

Jin, Xin published the artcileDesign, synthesis, and anticancer activity of novel berberine derivatives prepared via CuAA C “click” chemistry as potential anticancer agents, Safety of 2-(Chloromethyl)benzonitrile, the publication is Drug Design, Development and Therapy (2014), 1047-1059, database is CAplus and MEDLINE.

A series of novel derivatives of phenyl-substituted berberine triazolyls has been designed and synthesized via copper-catalyzed azide-alkyne cycloaddition click chem. in an attempt to develop antitumor agents. All of the compounds were evaluated for anticancer activity against a panel of three human cancer cell lines, including MCF-7 (breast), SW-1990 (pancreatic), and SMMC-7721 (liver) and the noncancerous human umbilical vein endothelial cell (HUVEC) cell lines. The results indicated that most of the compounds displayed notable anticancer activities against the MCF-7 cells compared with berberine. Among these derivatives, compound 16 showed the most potent inhibitory activity against the SW-1990 and SMMC-7721 cell lines, with half-maximal inhibitory concentration (IC₅₀) values of 8.54±1.97 μM and 11.87±1.83 μM, resp. Compound 36 exhibited the most potent inhibitory activity against the MCF-7 cell line, with an IC₅₀ value of 12.57±1.96 μM. Compound 16 and compound 36 exhibited low cytotoxicity in the HUVEC cell line, with IC₅₀ values of 25.49±3.24 μM and 30.47±3.47 μM. Furthermore, compounds 14, 15, 16, 17, 18, 32, and 36 exhibited much better selectivity than berberine toward the normal cell line HUVEC.

Drug Design, Development and Therapy 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, Safety of 2-(Chloromethyl)benzonitrile.

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