Month: November 2022

Huamani, Luis Enrique Santa Cruz published the artcileRole of Protonation and Isomerism in the Supramolecular Architectures of Heteroaryl-2-imidazole Compounds: Crystal Packing Patterns and Energetics, Name: Picolinonitrile, the main research area is azaarylimidazole isomer crystal structure packing protonation.

The influence of isomerism and protonation on crystal packing patterns of three isomeric heteroaryl-2-imidazoles and one related compound was investigated by using single-crystal X-ray diffraction and d. functional theory. The comparison of their crystal structures helped unveil the details of the energetic balance controlling supramol. packing and an unprecedented supramol. synthon. The neutral species were featured by a whole crystal close packing like a herringbone pattern, which was mainly favored by C-H···π interactions. On the other hand, the crystal packing of the protonated species was characterized by π-stacking layers being supported by π···π and anion-π interactions. Energy framework anal. revealed that both Coulombic interactions between hydrogen bond chains and dispersion energies mainly contributed to the stabilization of the herringbone pattern assembly, whereas a predominant contribution from Coulombic energy frameworks to total energy in protonated forms was observed The different patterns displayed pieces of evidence of not only the important participation of the heteroaryl moieties in the supramol. assembly but also the significant contribution of protonation hampering the N-H···N hydrogen bonding interactions in the imidazole group. A thorough characterization of the compounds by means of thermogravimetric anal., differential scanning calorimetry, Fourier-transform IR spectroscopy, NMR, and electrospray ionization-(+)-MS is also presented. The most characteristic crystal packing patterns of a series of N-heteroaryl-2-imidazole systems has been observed and analyzed. Neutral forms tend to pack in a herringbone pattern, whereas protonated forms tend to pack in parallel π-stacked layers. The imidazole fragments dominate the construction of the supramol. architectures through complex hydrogen bond networks. An unprecedented supramol. synthon was also found for one of the supramol. arrangements, and the energetics involved in the crystal packings was also assessed by theor. methods.

Crystal Growth & Design published new progress about Amines, salts Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Name: Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

O’Broin, Calvin Q. published the artcileSynthesis of 2-Amino-1,3-dienes from Propargyl Carbonates via Palladium-Catalyzed Carbon-Nitrogen Bond Formation, SDS of cas: 1885-29-6, the main research area is amine propargyl carbonate palladium catalyst carbon nitrogen bond dienylation; amino diene preparation.

A catalytic method to synthesize 1,3,-dienes from propargylic precursors is reported. This palladium-catalyzed carbon-nitrogen bond-forming reaction furnishes 2-amino-1,3-dienes in excellent yields (up to 98%) and shows a broad tolerance to functional group diversity. The reaction has been demonstrated for over 30 amine substrates, including anilines and indoles, and proceeds under mild neutral conditions. The resulting 1,3-dienes are of great synthetic interest because of their further reaction potential.

Organic Letters published new progress about Alkenylation (decarboxylative dienylation). 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, SDS of cas: 1885-29-6.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Kalashnikov, Valery V. published the artcile5-Phenyl- and 5,10-diphenyltetrabenzoporphyrins: Novel synthetic approach, physicochemical study with an emphasis on NMR spectroscopy, and identification of benzylated derivatives, COA of Formula: C8H4N2, the main research area is tetrabenzoporphyrin phenyl preparation NMR UV VIS.

Novel synthetic approach to low-symmetry meso-Ph substituted tetrabenzoporphyrins (TPBs) by Zn(OAc)2 templated assembly of phthalonitrile in the presence of benzyltriphenylphosphonium chloride has been proposed affording two main products: 5-phenyl-21H,23H-TBP (I) and 5,10-diphenyl-21H,23H-TBP (II) with higher yield for compound I. Procedure for isolation of I and II in individual high purity state has been developed supplemented with selection of an appropriate NMR solvent system (CDCl3 with 1% additive of CF3COOH) that allowed full signal assignment in 1H and 13C spectra to be made utilizing homonuclear 1H-1H (COSY, NOESY, TOCSY) and heteronuclear 1H-13C (HSQC) correlation techniques. Isolation and physicochem. study of a mixture of monobenzylated co-products were carried out as well involving 1D and 2D NMR spectroscopies, which for the first time allowed not only to find out their structure, but also to determine the ratio of the positional isomers formed.

Dyes and Pigments published new progress about NMR (nuclear magnetic resonance). 91-15-6 belongs to class nitriles-buliding-blocks, name is Phthalonitrile, and the molecular formula is C8H4N2, COA of Formula: C8H4N2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Shigeno, Masanori published the artcileDirect C-H carboxylation forming polyfunctionalized aromatic carboxylic acids by combined Bronsted bases, Related Products of nitriles-buliding-blocks, the main research area is polyfunctionalized methyl benzoate preparation; arene carbon dioxide carboxylation Bronsted base promoted.

CO2 fixation into electron-deficient aromatic C-H bonds proceeded with the combined Bronsted bases LiO-t-Bu and LiO-t-Am/CsF/18-crown-6 (t-Am = CEtMe2) under a CO2 atmosphere to afford a variety of polyfunctionalized aromatic carboxylic acid derivatives RCO2Me [R = 2,4,6-tri-BrC6H2, 2,3-di-ClC6H3, 2-O2NC6H4, etc.].

Organic Letters published new progress about Aromatic hydrocarbons Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 91-15-6 belongs to class nitriles-buliding-blocks, name is Phthalonitrile, and the molecular formula is C8H4N2, Related Products of nitriles-buliding-blocks.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Chen, Ying published the artcileAssembly of α-(Hetero)aryl Nitriles via Copper-Catalyzed Coupling Reactions with (Hetero)aryl Chlorides and Bromides, Formula: C16H13NO, the main research area is aryl heteroaryl nitrile synthesis; copper catalyzed coupling decarboxylation aryl heteroaryl halide cyanoacetate; C−C cross-coupling; anti-inflammatory drugs; copper; oxalamide ligands; α-(hetero)aryl nitriles.

α-(Hetero)aryl nitriles are important structural motifs for pharmaceutical design. The known methods for direct synthesis of these compounds via coupling with (hetero)aryl halides suffer from narrow reaction scope. Herein, we report that the combination of copper salts and oxalic diamides enables the coupling of a variety of (hetero)aryl halides (Cl, Br) and Et cyanoacetate under mild conditions, affording α-(hetero)arylacetonitriles via one-pot decarboxylation. Addnl., the CuBr/oxalic diamide catalyzed coupling of (hetero)aryl bromides with α-alkyl-substituted Et cyanoacetates proceeds smoothly at 60°C, leading to the formation of α-alkyl (hetero)arylacetonitriles after decarboxylation. The method features a general substrate scope and is compatible with various functionalities and heteroaryls. Thus, e.g., 4-chloroanisole + Et cyanoacetate → 2-(4-methoxyphenyl)acetonitrile (up to 80%).

Angewandte Chemie, International Edition published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent) (and heteroaryl). 42872-30-0 belongs to class nitriles-buliding-blocks, name is 2-(3-Benzoylphenyl)propanenitrile, and the molecular formula is C16H13NO, Formula: C16H13NO.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mashweu, Adelaide R. published the artcileSubstrate profiling of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870, Name: 2-Aminobenzonitrile(Flakes or Chunks), the main research area is substrate profiling cobalt nitrile hydratase Rhodococcus rhodochrous ATCCBAA 870; biocatalysis; carboxamide; green chemistry; nitrile hydratase.

The aromatic substrate profile of the cobalt nitrile hydratase from Rhodococcus rhodochrous ATCC BAA 870 was evaluated against a wide range of nitrile containing compounds (>60). To determine the substrate limits of this enzyme, compounds ranging in size from small (90 Da) to large (325 Da) were evaluated. Larger compounds included those with a bi-aryl axis, prepared by the Suzuki coupling reaction, Morita-Baylis-Hillman adducts, heteroatom-linked diarylpyridines prepared by Buchwald-Hartwig cross-coupling reactions and imidazo[1,2-a]pyridines prepared by the Groebke-Blackburn-Bienayme multicomponent reaction. The enzyme active site was moderately accommodating, accepting almost all of the small aromatic nitriles, the diarylpyridines and most of the bi-aryl compounds and Morita-Baylis-Hillman products but not the Groebke-Blackburn-Bienayme products. Nitrile conversion was influenced by steric hindrance around the cyano group, the presence of electron donating groups (e.g., methoxy) on the aromatic ring, and the overall size of the compound

Molecules published new progress about Baylis-Hillman reaction. 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Name: 2-Aminobenzonitrile(Flakes or Chunks).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Mikshiev, Vladimir Y. published the artcileperi-Interactions in 1,8-bis(dimethylamino)naphthalene ortho-ketimine cations facilitate [1,5]-hydride shift: selective synthesis of 1,2,3,4-tetrahydrobenzo[h]quinazolines, Recommanded Product: Picolinonitrile, the main research area is selective tetrahydrobenzoquinazoline preparation density functional theory; bis dimethylamino naphthalene ketimine heterocyclization.

Selective heterocyclization leading to 1,2,3,4-tetrahydrobenzo[h]quinazolines I (R1 = H, Br; R2 = Ph, n-Bu, furan-2-yl, etc.) from ortho-ketimines of 1,8-bis(dimethylamino)naphthalene (DmanIms) II under acid catalysis has been revealed. In contrast to the rather unreactive N,N-dimethylaniline ortho-ketimine II, DmanIms readily undergo this transformation without an addnl. catalyst. This distinction in the reactivity underscores the importance of the second peri-NMe2 group in DmanIms, which facilitates a [1,5]-hydride shift and the subsequent cyclization. The cascade of peri-interactions emerging between 1-NMe2 and 8-NMe2 groups has been identified as a reason for the catalytic effect: (1) the hydrogen bond in the DmanIm dication constrains 1-NMe2 in the desired position providing proximity of reaction centers, (2) the repulsion of the lone pairs of 8-NMe2 group and unrelaxed 1-NMe2 group arising right after deprotonation process reduces the Gibbs free energy of activation (ΔG) for the straight hydride shift, and (3) the electrostatic interaction between 8-NMe2 and the charged N=CH2+ group in the intermediate increases the ΔG for the reverse hydride shift.

Organic & Biomolecular Chemistry published new progress about Density functional theory, B3LYP. 100-70-9 belongs to class nitriles-buliding-blocks, name is Picolinonitrile, and the molecular formula is C6H4N2, Recommanded Product: Picolinonitrile.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Liu, Fusheng published the artcileSuccinimide-Based Ionic Liquids: An Efficient and Versatile Platform for Transformation of CO2 into Quinazoline-2,4(1H,3H)-diones under Mild and Solvent-Free Conditions, Safety of 2-Aminobenzonitrile(Flakes or Chunks), the main research area is aminobenzonitrile carbon dioxide succinimide based ionic liquid cyclocondensation catalyst; quinazolinedione preparation green chem.

Multifunctional succinimide-based ionic liquids (SIILs) were well-designed and synthesized, and they were used as a dual solvent-catalyst for efficient transformation of CO2 and 2-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones under mild conditions. The catalytic behaviors, including the effects of anion-cation structures and reaction parameters, catalyst recyclability, and versatility were thoroughly studied. The optimum [HTMG][Suc] comprising a tetramethylguanidine cation and a succinimide anion showed excellent activity toward various substituted 2-aminobenzonitrile substrates. [HTMG][Suc] was easily recyclable with superior structural integrity. The possible pathways of CO2 and 2-aminobenzonitrile activated by [HTMG][Suc] were investigated in depth, which supported the reaction mechanism well. In comparison with reported catalysts, the protocol herein exhibited comparable catalytic performance under milder and greener conditions without any addnl. organic solvents.

ACS Sustainable Chemistry & Engineering published new progress about Cyclocondensation reaction. 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Safety of 2-Aminobenzonitrile(Flakes or Chunks).

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Fan, Zhenhua published the artcileMetal-free synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade michael addition / cyclization of methyl-4,4-difluorobut-2-ynoate with 2-aminobenzonitriles, Formula: C7H6N2, the main research area is difluoromethylated quinoline preparation DBU michael cyclization methyl difluorobutynoate aminobenzonitrile.

A facile synthesis of 2-difluoromethylated quinolines via DBU-promoted cascade Michael addition/cyclization between functionalized 2-aminobenzonitriles and Me 4,4-difluorobut-2-ynoate was developed. Various highly functionalized quinolines were assembled in moderate to good yields under mild metal-free reaction conditions.

Tetrahedron published new progress about Crystal structure. 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Formula: C7H6N2.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zhang, Xiaheng published the artcileCopper-mediated synthesis of drug-like bicyclopentanes, Computed Properties of 1885-29-6, the main research area is bicyclopentane preparation copper iridium catalyst propellane nucleophile radical.

Multicomponent reactions are relied on in both academic and industrial synthetic organic chem. owing to their step- and atom-economy advantages over traditional synthetic sequences1. Recently, bicyclo[1.1.1]pentane (BCP) motifs have become valuable as pharmaceutical bioisosteres of benzene rings, and in particular 1,3-disubstituted BCP moieties have become widely adopted in medicinal chem. as para-Ph ring replacements2. These structures are often generated from [1.1.1]propellane via opening of the internal C-C bond through the addition of either radicals or metal-based nucleophiles3-13. The resulting propellane-addition adducts are then transformed to the requisite polysubstituted BCP compounds via a range of synthetic sequences that traditionally involve multiple chem. steps. Although this approach was effective so far, a multicomponent reaction that enables single-step access to complex and diverse polysubstituted drug-like BCP products would be more time efficient compared to current stepwise approaches. Here the authors report a one-step three-component radical coupling of [1.1.1]propellane to afford diverse functionalized bicyclopentanes using various radical precursors and heteroatom nucleophiles via a metallaphotoredox catalysis protocol. This copper-mediated reaction operates on short timescales (five minutes to one hour) across multiple (more than ten) nucleophile classes and can accommodate a diverse array of radical precursors, including those that generate alkyl, α-acyl, trifluoromethyl and sulfonyl radicals. This method was used to rapidly prepare BCP analogs of known pharmaceuticals, one of which is substantially more metabolically stable than its com. progenitor.

Nature (London, United Kingdom) published new progress about Electrochemical redox reaction. 1885-29-6 belongs to class nitriles-buliding-blocks, name is 2-Aminobenzonitrile(Flakes or Chunks), and the molecular formula is C7H6N2, Computed Properties of 1885-29-6.

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts