Tag: 200-300

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

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Spectrographic method for the detection of active methylene groups and synthesis of several styrene and stilbene derivatives. VI. Amino derivatives of phenylacetonitrile was written by Boyer, Jacqueline;Bruylants, Albert. And the article was included in Bulletin de la Societe Chimique de France in 1958.Product Details of 67197-53-9 This article mentions the following:

The reactivity of m- and p-amino derivatives of PhCH₂CN in condensations with BzH and its p-NMe₂ derivative decreases with decreasing acidity of the CH₂CN group. The order of acidity produced by the following substituents in PhCH₂CN, as determined by comparison of spectra in EtOH and EtONa, is: H ∼ p-Me₃NI ∼ m-Me₃NI ≫ p-NH₂ > m-NH₂ > p-Me₂N ≫ m-Me₂N. Changes in spectra with time in EtONa show that the ionization of the last four of these is slow. The m- and p-NH₂ derivatives react with BzH and p-Me₂NC₆H₄CHO to yield principally the azomethines, but the other compounds give high yields of α-cyanostilbenes after 40 hrs. in alc. EtONa. The following cyanostilbenes, XC₆H₄C(CN):CHC₆H₄Y, were obtained (X, Y, yield, and m.p. are given): p-Me₃NI, H, 85, 175-98° (geometric isomers); p-Me₃NI, p-NMe₂, 87, 195-6.5°; p-Me₂N, H, 87, 136-7°; p-Me₂N, p-NMe₂, 85, 196-7.5°; m-Me₃NI, H, 88, 172-97° (geometric isomers); m-Me₃NI, p-NMe₂, 92, 161-2°; m-Me₂N, H, 90, -; m-Me₂N, p-NMe₂, 88, 117-208°. The p-H₂NC₆H₄CH₂CN and its m-isomer, b₈ 179-80° (HCl salt, m. 199-201°), were prepared by reduction of the corresponding nitro compounds with SnCl₂, quaternized with MeI to the p-Me₃NI, m. 167-8°, and m-Me₃NI, m. 173-4°, derivatives resp., and these were demethylated to p-Me₂NC₆H₄CH₂CN, m. 53.5-55°, and its m-isomer, m. 173-4°, resp. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9Product Details of 67197-53-9).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Product Details of 67197-53-9

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One-pot synthesis of secondary amines from alcohols and nitroarenes on TiO₂ loaded with Pd nanoparticles under UV irradiation was written by Selvam, Kaliyamoorthy;Sakamoto, Hirokatsu;Shiraishi, Yasuhiro;Hirai, Takayuki. And the article was included in New Journal of Chemistry in 2015.Product Details of 10282-32-3 This article mentions the following:

Photoirradiation (λ > 300 nm) of TiO₂ loaded with Pd nanoparticles (2%, ∼5 nm diameter) in water containing benzyl alc. and nitrobenzene at room temperature successfully produces the corresponding secondary amine (N-benzylaniline) with 96% yield. This is achieved via three consecutive catalytic reactions: (i) photocatalytic oxidation of alc. (aldehyde formation) and reduction of nitrobenzene (aniline formation); (ii) catalytic condensation of the formed aldehyde with aniline on the TiO₂ surface (imine formation); and, (iii) photocatalytic hydrogenation of the formed imine (secondary amine formation). This catalytic system successfully produces several kinds of secondary amines, even those containing reducible substituents such as -CN, -COOH, or -CHO with >76% yields. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Product Details of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Product Details of 10282-32-3

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A novel multiple-stage antimalarial agent that inhibits protein synthesis was written by Baragana, Beatriz;Hallyburton, Irene;Lee, Marcus C. S.;Norcross, Neil R.;Grimaldi, Raffaella;Otto, Thomas D.;Proto, William R.;Blagborough, Andrew M.;Meister, Stephan;Wirjanata, Grennady;Ruecker, Andrea;Upton, Leanna M.;Abraham, Tara S.;Almeida, Mariana J.;Pradhan, Anupam;Porzelle, Achim;Martinez, Maria Santos;Bolscher, Judith M.;Woodland, Andrew;Luksch, Torsten;Norval, Suzanne;Zuccotto, Fabio;Thomas, John;Simeons, Frederick;Stojanovski, Laste;Osuna-Cabello, Maria;Brock, Paddy M.;Churcher, Tom S.;Sala, Katarzyna A.;Zakutansky, Sara E.;Jimenez-Diaz, Maria Belen;Sanz, Laura Maria;Riley, Jennifer;Basak, Rajshekhar;Campbell, Michael;Avery, Vicky M.;Sauerwein, Robert W.;Dechering, Koen J.;Noviyanti, Rintis;Campo, Brice;Frearson, Julie A.;Angulo-Barturen, Inigo;Ferrer-Bazaga, Santiago;Gamo, Francisco Javier;Wyatt, Paul G.;Leroy, Didier;Siegl, Peter;Delves, Michael J.;Kyle, Dennis E.;Wittlin, Sergio;Marfurt, Jutta;Price, Ric N.;Sinden, Robert E.;Winzeler, Elizabeth A.;Charman, Susan A.;Bebrevska, Lidiya;Gray, David W.;Campbell, Simon;Fairlamb, Alan H.;Willis, Paul A.;Rayner, Julian C.;Fidock, David A.;Read, Kevin D.;Gilbert, Ian H.. And the article was included in Nature (London, United Kingdom) in 2015.Formula: C12H14N2O This article mentions the following:

There is an urgent need for new drugs to treat malaria, with broad therapeutic potential and novel modes of action, to widen the scope of treatment and to overcome emerging drug resistance. Here we describe the discovery of DDD107498, a compound with a potent and novel spectrum of antimalarial activity against multiple life-cycle stages of the Plasmodium parasite, with good pharmacokinetic properties and an acceptable safety profile. DDD107498 demonstrates potential to address a variety of clin. needs, including single-dose treatment, transmission blocking and chemoprotection. DDD107498 was developed from a screening program against blood-stage malaria parasites; its mol. target has been identified as translation elongation factor 2 (eEF2), which is responsible for the GTP-dependent translocation of the ribosome along mRNA, and is essential for protein synthesis. This discovery of eEF2 as a viable antimalarial drug target opens up new possibilities for drug discovery. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Formula: C12H14N2O

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Exploring Homogeneous Conditions for Mild Buchwald-Hartwig Amination in Batch and Flow was written by Kashani, Saeed K.;Jessiman, Jacob E.;Newman, Stephen G.. And the article was included in Organic Process Research & Development in 2020.Name: 4-(Benzylamino)benzonitrile This article mentions the following:

The use of high throughput experimentation to identify a number of conditions that enable Buchwald-Hartwig reactions to be carried out using readily available ligands (e.g. XantPhos) with DBU as a soluble, functional group tolerant, homogeneous base was described. Application of this system to diverse aminations in batch and flow were demonstrated, as was the translation of this technique to performing continuous Mizoroki-Heck and Sonogashira coupling reactions. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Name: 4-(Benzylamino)benzonitrile).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. The electronic structure of nitriles is very similar to that of an alkyne with the main difference being the presence of a set of lone pair electrons on the nitrogen. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Name: 4-(Benzylamino)benzonitrile

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Superacidic Cyclization of Activated Anthranilonitriles into 2-Unsubstituted-4-aminoquinolines was written by Lavrard, Hubert;Larini, Paolo;Popowycz, Florence. And the article was included in Organic Letters in 2017.Category: nitriles-buliding-blocks This article mentions the following:

4-Aminoquinolines were prepared in a three-step synthesis starting from substituted anthranilonitriles. The condensation on 1,1,1-trichloro-4-ethoxybut-3-enone proceeded efficiently either neat or in refluxing EtOH. Cyclization in superacidic trifluoromethanesulfonic acid provided unstable intermediate, which upon treatment with NaOEt in ethanol, afforded the expected esters. Theor. investigations pointed out a monoprotonated nitrilium as the reactive species during the cyclization process. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Category: nitriles-buliding-blocks).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
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N-Alkylation of aniline derivatives by use of potassium cation-exchanged Y-type zeolite was written by Onaka, Makoto;Umezono, Akihiro;Kawai, Motomitsu;Izumi, Yusuke. And the article was included in Journal of the Chemical Society, Chemical Communications in 1985.Formula: C14H12N2 This article mentions the following:

Zeolite K-Y effectively promoted the N-alkylation of p-RC₆H₄NH₂ (R = NO₂, CN, CO₂Et, H, Cl, Me) with R¹Br (R¹ = CH₂CH:CH₂, CH₂Ph) or Me₂SO₄ in PhMe or C₆H₆ at 50°-reflux for 5-15 h to give 55-90% yield of 3.9-50:1 mixtures of p-RC₆H₄NHR¹ and p-RC₆H₄NR¹₂ (R as before, R¹ = CH₂CH:CH₂, CH₂Ph, Me). Results were compared with those for the analogous γ-alumina-promoted alkylation. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Formula: C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. 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.Formula: C14H12N2

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Synthesis of substituted thieno[2,3-b]pyrroles was written by Wei, Hongtao;Cai, Jin;Sun, Min;Ji, Min. And the article was included in Heteroatom Chemistry in 2007.Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Thieno[2,3-b]pyrroles were synthesized through three steps: Gewald synthesis, alkylation, and Thorpe-Ziegler cyclization. Di-Et 3,6-bis((ethoxycarbonyl)methyl)-4-amino-6H-thieno-[2,3-b]pyrrole-2,5- dicarboxylate was obtained by one-pot method in DMF in good yield and high quality. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) 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. Alkyl nitriles are sufficiently acidic to undergo deprotonation of the C-H bond adjacent to the CN group.Strong bases are required, such as lithium diisopropylamide and butyl lithium. The product is referred to as a nitrile anion. Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate

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Platinum Assisted Tandem P-C Bond Cleavage and P-N Bond Formation in Amide Functionalized Bisphosphine o-Ph₂PC₆H₄C(O)N(H)C₆H₄PPh₂-o: Synthesis, Mechanistic, and Catalytic Studies was written by Kunchur, Harish S.;Balakrishna, Maravanji S.. And the article was included in Inorganic Chemistry in 2022.Computed Properties of C14H12N2 This article mentions the following:

The reactions of amide functionalized bisphosphine o-Ph₂PC₆H₄C(O)N(H)C₆H₄PPh₂-o (1) with Pt salts is described. Treatment of 1 with [Pt(COD)Cl₂] yielded a chelate complex, [PtCl₂{o-Ph₂PC₆H₄C(O)N(H)C₆H₄PPh₂-o}κ²-P,P] (2), which on subsequent treatment with LiHMDS formed a novel 1,2-azaphospholene-phosphine complex [PtPhCl{o-C₆H₄{C(O)N(o-PPh₂(C₆H₄))P(Ph)}}κ²-P,P] (3) involving a tandem P–C bond cleavage and P-N bond formation. The same complex 3 on passing dry HCl gas afforded dichloro-complex [PtCl₂{o-C₆H₄{C(O)N(o-PPh₂(C₆H₄))P(Ph)}}κ²-P,P] (5). Complex 2 upon refluxing in toluene or treatment of 1 with [Pt(COD)Cl₂] in the presence of a base at room temperature resulted in pincer complex [PtCl{o-Ph₂PC₆H₄C(O)N(C₆H₄PPh₂-o)}κ³-P,N,P] (4). Reaction of 1 with [Pt(COD)ClMe] at room temperature also afforded the pincer complex [PtMe{o-Ph₂PC₆H₄C(O)N(C₆H₄PPh₂-o)}κ³-P,N,P] (6). Mechanistic studies on 1,2-azaphospholene formation showed the reductive elimination of LiCl to form a phosphonium salt that readily adds one of the P-C bonds oxidatively to the in situ generated Pt⁰ species to form a chelate complex 3. Analogous Pd complex [PdCl₂{o-C₆H₄{C(O)N(o-PPh₂(C₆H₄))P(Ph)}}κ²-P,P] (7) showed excellent catalytic activity toward N-alkylation of amines with alcs. with a very low catalyst loading (0.05 mol %), and the methodol. is very efficient toward the gram scale synthesis of many N-alkylated amines. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Computed Properties of C14H12N2).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Computed Properties of C14H12N2

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Nitriles – Chemistry LibreTexts

Density function theory study on anthracene substituted by dicyanovinyl in different positions was written by Zhang, Jinglai;Miao, Tifang;Wang, Hua;Tian, Anmin. And the article was included in Huaxue Tongbao in 2003.Application of 55490-87-4 This article mentions the following:

Results of RHF(RHF) and d. function theory(DFT) calculations are reported for 2-dicyanovinyl anthracene(2-DCVA) and 9-dicyanovinyl anthracene(9-DCVA) at B3LYP/6-311+G(d,p)//RHF/6-31G(d,p) level. The equilibrium geometries of 2-DCVA and 9-DCVA have been optimized and the harmonic vibrational frequencies have been calculated The calculating results show that the ground state of 9-DCVA is higher than that of 2-DCVA in total energy. Having revolved angles between anthracene and dicyanovinyl from -180.0° to 180.0°, their potential energy curves are obtained to find their equilibrium geometries, The results show that there are two different stable geometries in energy and a transition geometry for 2-DCVA while there are a stable geometry and two transition geometries for 9-DCVA, the structure of 2-DCVA is more planar than 9-DCVA. At PM3/CIS level, their electronic spectrum were calculated and the vertical excitation energies and corresponding oscillator strengths from the ground states to the excited states are obtained. These results are in good agreement with the results obtained from experiment In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Application of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. 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 of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts