Month: February 2023

Engineering a Nanoscale Primary Amide-Functionalized 2D Coordination Polymer as an Efficient and Recyclable Heterogeneous Catalyst for the Knoevenagel Condensation Reaction was written by Markad, Datta;Khullar, Sadhika;Mandal, Sanjay K.. And the article was included in ACS Applied Nano Materials in 2018.Related Products of 55490-87-4 This article mentions the following:

This work reports the design, structural characterization and catalytic behavior of the first example of primary amide- functionalized coordination polymers (CPs), namely {[Cd₂(2-bpbg)(fum)₂(H₂O)₂]·8.5H₂O}_n (1) (where, 2-bpbg = N,N’-bis(2-pyridylmethyl)-1,4-diaminobutane-N,N’-diacetamide and fum = fumarate). CP 1 was synthesized from a one-pot self-assembly of starting materials in methanol under ambient conditions in excellent yield and purity, allowing an easy access to multi-gram quantities of it within few hours. As an example, CP 1 has been used as a highly efficient heterogeneous catalyst in the carbon-carbon bond forming Knoevenagel condensation reaction for the conversion of benzaldehyde to benzylidene malononitrile. CP 1 possesses both Lewis acidic and Bronsted basic character for the presence of unsaturated metal sites and primary amide groups, resp., making it a highly competent bifunctional catalyst for such type of reactions. Surprisingly, 100% conversion was observed using only 2 mol% catalyst within 1 h at 27° in methanol. However, 2 mol% and 3 mol% catalyst loadings but without a solvent gives 93% and 100% conversions, resp., in 1 h at 27°. CP 1 is far better than those reported in the literature so far. To prove the uniqueness and efficiency of the primary amide based ligand, a similar compound with a pyridyl-based ligand was also synthesized, {[Cd₂(tpbn)(fum)₂]·6H₂O}_n (2) (where, tpbn = N’,N’,N”,N”-tetrakis(pyridin-2-ylmethyl)butane-1,4-diamine). Using CP 2 under the same catalyst loading and conditions (2 mol%, 27°, 1 h), only 28% conversion was observed Selective heterogeneous catalytic properties of 1 over 2 are due to the presence of the primary amide moieties and open metal sites. Moreover, CP 1 can easily be separated from the reaction mixture and reused for five consecutive cycles without significant loss of its activity. Both 1 and 2 were fully characterized by elemental anal., IR spectroscopy, TGA and single crystal and powder x-ray diffraction. These crystallize in the triclinic P1 space group, showing their isostructural nature and 3-connected, uninodal {63}-hcb net topol. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Related Products of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Related Products of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Base-Mediated Amination of Alcohols Using Amidines was written by Zhang, Chunyan;Li, Zehua;Chen, Jianbin;Qi, Shuo;Fang, Yanchen;Zhang, Sheng;Ren, Chaoyu;Lu, Fenghong;Liang, Zuyu;Jiang, Shaohua;Jia, Xiaofei;Yu, Shuangming;Zhang, Guoying. And the article was included in Journal of Organic Chemistry in 2020.Synthetic Route of C14H12N2 This article mentions the following:

Novel and efficient base-mediated N-alkylation and amidation of amidines with alcs. have been developed, which can be carried out in one-pot reaction conditions, which allows for the synthesis of a wide range of N-alkyl amines and free amides in good to excellent yields with high atom economy. In contrast to borrowing hydrogen/hydrogen autotransfer or oxidative-type N-alkylation reactions, in which alcs. are activated by transition-metal-catalyzed or oxidative aerobic dehydrogenation, the use of amidines provides an effective surrogate of amines. This circumvents the inherent necessity in N-alkylation of an oxidant or a catalyst to be stabilized by ligands. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Synthetic Route of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Synthetic Route of C14H12N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Polystyrene-Supported Palladium (Pd@PS)-Catalyzed Carbonylative Annulation of Aryl Iodides Using Oxalic Acid as a Sustainable CO Source for the Synthesis of 2-Aryl Quinazolinones was written by Ram, Shankar;Shaifali;Chauhan, Arvind Singh;Sheetal;Sharma, Ajay Kumar;Das, Pralay. And the article was included in Chemistry – A European Journal in 2019.Reference of 1483-54-1 This article mentions the following:

An efficient and convenient strategy for the synthesis of diversely substituted quinazolinones from o-carbamoyl/cyano aniline and aryl iodides using oxalic acid as a CO source under polystyrene supported palladium (Pd@PS) nanoparticles (NPs) catalyzed conditions was developed. The oxalic acid were employed as safe, economic, environmentally benign, sustainable and bench-stable, solid CO surrogate under Double-Layer-Vial (DLV) system for the synthesis of 2-aryl quinazolinones. This methodol. does not require any special high-pressure equipment like autoclaves, microwaves, etc. Moreover, a simple procedure for catalyst preparation, catalyst recyclability, easy handling of reaction, additive and base-free generation of CO, excellent to good yields and vast substrate scope were the addnl. features of developed protocol. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Reference of 1483-54-1).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Reference of 1483-54-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

The comparison of molecular surfaces by neural networks and its applications to quantitative structure activity studies was written by Polanski, Jaroslaw;Gasteiger, Johann;Wagener, Markus;Sadowski, Jens. And the article was included in Quantitative Structure-Activity Relationships in 1998.Application In Synthesis of 3-Amino-4-methoxybenzonitrile This article mentions the following:

Self-organizing Kohonen neural networks are used to obtain quant. structure-activity relationships. Simple mols. were selected to discuss the essential features of the transformation. Descriptors calculated from maps obtained from comparative studies with template mols. applied to the anal. of compounds derived from butane, as well as Et carboxylates and nitroanilines and aminobenzonitriles (sweet-tasting compounds) can be correlated with various mol. effects. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Application In Synthesis of 3-Amino-4-methoxybenzonitrile).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitrile function is a very important functional group because it can be manipulated to other functional groups such as carboxylic acid by hydrolysis or amine by reduction, respectively. Nitriles are susceptible to hydrogenation over diverse metal catalysts. The reaction can afford either the primary amine (RCH2NH2) or the tertiary amine ((RCH2)3N), depending on conditions.Application In Synthesis of 3-Amino-4-methoxybenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Silica-sulfuric acid: novel, simple, efficient and reusable catalyst for hydration of nitrile to amide was written by Chandrashekharappa, Sandeep;Venugopala, Katharigatta N.;Venugopala, Rashmi;Odhav, Bharti. And the article was included in Asian Journal of Chemistry in 2016.Reference of 60979-25-1 This article mentions the following:

Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatog. method and characterized by ¹H NMR, ¹³C NMR and mass spectral anal. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methoxybenzonitrile (cas: 60979-25-1Reference of 60979-25-1).

3-Amino-4-methoxybenzonitrile (cas: 60979-25-1) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Reference of 60979-25-1

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

First Gewald reaction ignited by sodium polysulfide: greener ultrasound-promoted synthesis of substituted 2-aminothiophenes in the absence of catalyst was written by Liang, Chengyuan;Lei, Dong;Wang, Xiuzhen;Zhang, Qingqing;Yao, Qizheng. And the article was included in Journal of Sulfur Chemistry in 2013.Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

In this paper, a modified and facile Gewald reaction triggered by sodium polysulfide in the absence of catalytic base was developed. This approach involves a one-pot ultrasound-irritated aqueous reaction between ketones or aldehydes, malononitrile and sodium sulfide [Na₂(S_x)] [sodium polysulfide, sodium sulfide [Na₂(S₄)], sodium sulfide [Na₂(S₆)], sodium sulfide (NaS)]. which are converted into the corresponding 2-aminothiophene derivatives in moderate to high yields. In comparison with conventional methods, the prominent features of this ultrasound-mediated procedure are exptl. simplicity, good functional group tolerance, atom efficiency, and the use of water as a green solvent. The title compounds thus formed included and amine nitrile [2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile] (I) and an analog, 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (II), 2-amino-4-ethyl-3-thiophenecarbonitrile, 2-amino-4-(phenylmethyl)-3-thiophenecarbonitrile. The synthesis of the target compounds was achieved using cyclohexanone, cyclopentanone, butanal, propanal, hexanal, benzeneacetaldehyde, benzenepropanal as starting materials. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Name: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Antituberculous compounds. XXII. Monoalkylaminobenzothioamides was written by Kakimoto, Shichiro;Tone, Ikuko. And the article was included in Journal of Medicinal Chemistry in 1965.Safety of 4-(Ethylamino)benzonitrile This article mentions the following:

Several monoalkyl, phenyl, and benzyl derivatives of 4-aminobenzothioamide, and their precursor nitriles were prepared to test the hypothesis that the extinction coefficient, Ε_maximum of the C-N stretching vibration in the ir adsorption spectrum of the parent nitrile parallels the inhibitory action against Mycobacterium tuberculosis strain H37Rv in vitro. No conclusions were drawn. In the experiment, the researchers used many compounds, for example, 4-(Ethylamino)benzonitrile (cas: 4714-63-0Safety of 4-(Ethylamino)benzonitrile).

4-(Ethylamino)benzonitrile (cas: 4714-63-0) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Safety of 4-(Ethylamino)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts