Category: 5153-73-1

Chen, Zhen published the artcileUse of a Traceless Activating and Directing Group for the Construction of Trifluoromethylpyrazoles: One-Pot Transformation of Nitroolefins and Trifluorodiazoethane, Quality Control of 5153-73-1, the publication is Angewandte Chemie, International Edition (2017), 56(16), 4569-4574, database is CAplus and MEDLINE.

We disclose an efficient one-pot transformation of trifluorodiazoethane and higher perfluorinated homologues with various nitroolefins. This method takes advantage of the nitro group as a traceless activating and directing group (TADG) that is released in the aromatization step to produce 4-substituted 3-perfluoroalkyl pyrazoles with complete regioselectivity [e.g, trans-β-nitrostyrene + CF₃CHN₂ → pyrazole I (89%) in presence of Ag₂O and Na₃PO₄]. The potential of this method is further demonstrated by the synthesis of penthiopyrad. Safety: 2,2,2-trifluorodiazoethane is potentially explosive.

Angewandte Chemie, International Edition 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, Quality Control of 5153-73-1.

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

Li, Miaomiao published the artcileTransition Metal-Free Oxidative Cross-Coupling Reaction of Activated Olefins with N-Alkyl Amides, Category: nitriles-buliding-blocks, the publication is Journal of Organic Chemistry (2021), 86(5), 3989-3998, database is CAplus and MEDLINE.

The K₂S₂O₈-mediated transition metal-free oxidative cross-coupling reaction of activated olefins with N-alkyl amides was developed, and the reaction gave N-allylic amides in moderate to good yield. This reaction protocol was suitable for different kinds of activated olefins.

Journal of Organic 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, Category: nitriles-buliding-blocks.

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

Chen, Zhen published the artcileTransition-Metal-Free [3 + 2] Cycloaddition of Nitroolefins and Diazoacetonitrile: A Facile Access to Multisubstituted Cyanopyrazoles, Synthetic Route of 5153-73-1, the publication is Organic Letters (2018), 20(7), 2120-2124, database is CAplus and MEDLINE.

Nitroalkenes such as β-nitrostyrenes (E)-RCH:CHNO₂ [R = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-Me₂NC₆H₄, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-F₃CC₆H₄, 4-NCC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 2-BrC₆H₄, 1-naphthyl, 2-naphthyl, 9-anthracenyl, 2-furyl, 2-thienyl, (E)-R¹CH:CH, PhCC, PhCH₂CH₂, Bu, i-Bu, cyclohexyl; R¹ = Ph, 4-MeOC₆H₄, 2-O₂NC₆H₄] underwent metal-free regioselective [3+2]-cycloaddition reactions with diazoacetonitrile N₂:CHCN either used sep. or generated in situ from aminoacetonitrile hydrochloride with Cs₂CO₃ in THF to give 3-pyrazolecarbonitriles such as I [R = Ph, 4-MeC₆H₄, 4-MeOC₆H₄, 4-Me₂NC₆H₄, 4-FC₆H₄, 4-ClC₆H₄, 4-BrC₆H₄, 4-F₃CC₆H₄, 4-NCC₆H₄, 3-MeOC₆H₄, 2-MeOC₆H₄, 2-BrC₆H₄, 1-naphthyl, 2-naphthyl, 9-anthracenyl, 2-furyl, 2-thienyl, (E)-R¹CH:CH, PhCC, PhCH₂CH₂, Bu, i-Bu, cyclohexyl; R¹ = Ph, 4-MeOC₆H₄, 2-O₂NC₆H₄] in 55-93% yields. The cycloaddition reaction was also performed in tandem with regioselective N-alkylation reactions with MeI or PhCH₂Br to yield 1-methyl- or 1-benzyl-3-pyrazolecarbonitriles in 31-73% yields with 10-48% of the 2-alkyl-3-pyrazolecarbonitrile regioisomers (<25% yields in ten of twelve cases). Diazoacetonitrile is potentially explosive and should be handled with caution.

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, Synthetic Route of 5153-73-1.

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

Li, Hua published the artcileModular Bifunctional Chiral Thioureas as Versatile Organocatalysts for Highly Enantioselective Aza-Henry Reaction and Michael Addition, HPLC of Formula: 5153-73-1, the publication is Advanced Synthesis & Catalysis (2012), 354(11-12), 2264-2274, S2264/1-S2264/57, database is CAplus.

A series of new modular bifunctional chiral thiourea organocatalysts were synthesized from natural Cinchona alkaloids and amino acids, and their performance in the aza-Henry reaction of nitroalkanes to imines, the Michael addition of acetylacetone to nitroolefins and the Michael addition of acetone to nitroolefins was investigated. Under the mild conditions, the important building blocks β-nitro amines and γ-nitro carbonyl compounds could be obtained in good yields (up to 95%) with excellent enantioselectivities (up to 99% ee) and diastereoselectivity (up to 17:1).

Advanced Synthesis & Catalysis 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, HPLC of Formula: 5153-73-1.

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

Cai, Shunyou published the artcileNew Approach to Oximes through Reduction of Nitro Compounds Enabled by Visible Light Photoredox Catalysis, Formula: C9H6N2O2, the publication is Organic Letters (2013), 15(11), 2660-2663, database is CAplus and MEDLINE.

A range of nitro compounds are smoothly reduced to their corresponding oximes under the synergistic effects of visible light irradiation, the Ru(bpy)₃Cl₂ photocatalyst, Huenig’s base, Mg(ClO₄)₂ activation, and MeCN solvent. This remarkably mild and environmentally benign protocol, when orchestrated with classical Beckmann rearrangement, enables such high-value industrial feedstock as caprolactam to be readily accessed from simple precursor nitrocyclohexane.

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, Formula: C9H6N2O2.

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

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

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

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

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