Tag: 200-300

Cp*Co(III) and Cu(OAc)₂ bimetallic catalysis for Buchwald-type C-N cross coupling of aryl chlorides and amines under base, inert gas & solvent-free conditions was written by Srivastava, Avinash K.;Sharma, Charu;Joshi, Raj K.. And the article was included in Green Chemistry in 2020.Formula: C14H12N2 This article mentions the following:

A strategy involving bimetallic catalysis with a combination of Cp*Co(CO)I₂ and Cu(OAc)₂ was used for performing Buchwald-type C-N coupling reactions of aryl chlorides RCl (R = Ph, pyridin-2-yl, 4-cyanophenyl, etc.) with amines R¹NHR² (R¹ = H, Et; R² = Pr, benzyl, 4-methoxyphenyl, etc.; R¹R² = -(CH₂)₄– and -(CH₂)₅-). The reactions proceeded at 100°C to produce excellent yields of many of the desired C-N coupled products R¹N(R)R², in 4 h, under aerobic reaction conditions. The reactions were shown to run under base-free and solvent-free conditions, enabling this strategy to work efficiently for electron-withdrawing and base-sensitive functionalities. The presented methodol. was found to be equally efficient for electron-donating functionalities as well as for primary (1°) and secondary (2°) aromatic and aliphatic amines. Moreover, the products were easily separated through the extractions of the organic aqueous layer, with this process chromatog. separations are not required. 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 carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Formula: C14H12N2

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Nitrile – Wikipedia,
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Identification, Design and Biological Evaluation of Heterocyclic Quinolones Targeting Plasmodium falciparum Type II NADH:Quinone Oxidoreductase (PfNDH2) was written by Leung, Suet C.;Gibbons, Peter;Amewu, Richard;Nixon, Gemma L.;Pidathala, Chandrakala;Hong, W. David;Pacorel, Benedicte;Berry, Neil G.;Sharma, Raman;Stocks, Paul A.;Srivastava, Abhishek;Shone, Alison E.;Charoensutthivarakul, Sitthivut;Taylor, Lee;Berger, Olivier;Mbekeani, Alison;Hill, Alasdair;Fisher, Nicholas E.;Warman, Ashley J.;Biagini, Giancarlo A.;Ward, Stephen A.;O’Neill, Paul M.. And the article was included in Journal of Medicinal Chemistry in 2012.Application In Synthesis of 4-(Morpholinomethyl)benzonitrile This article mentions the following:

Following a program undertaken to identify hit compounds against NADH:ubiquinone oxidoreductase (PfNDH2), a novel enzyme target within the malaria parasite Plasmodium falciparum, hit to lead optimization led to identification of CK-2-68, a mol. suitable for further development. To reduce ClogP and improve solubility of CK-2-68 incorporation of a variety of heterocycles, within the side chain of the quinolone core, was carried out, and this approach led to a lead compound SL-2-25 (I). I has IC₅₀s in the nanomolar range vs. both the enzyme and whole cell P. falciparum (IC₅₀ = 15 nM PfNDH2; IC₅₀ = 54 nM (3D7 strain of P. falciparum)) with notable oral activity of ED₅₀/ED₉₀ of 1.87/4.72 mg/kg vs. Plasmodium berghei (NS Strain) in a murine model of malaria when formulated as a phosphate salt. Analogs in this series also demonstrate nanomolar activity against the bc₁ complex of P. falciparum providing the potential added benefit of a dual mechanism of action. The potent oral activity of 2-pyridyl quinolones underlines the potential of this template for further lead optimization studies. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Application In Synthesis of 4-(Morpholinomethyl)benzonitrile).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) 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.Application In Synthesis of 4-(Morpholinomethyl)benzonitrile

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Synthesis of 2-azo-3-cyano-5-carbethoxy thiophene derivatives and their application on polyester fibers was written by Sabnis, Ram W.;Rangnekar, Dinesh W.. And the article was included in Journal of Chemical Technology and Biotechnology in 1990.Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Synthesis of 2-(hetaryl or aryl)-azo thiophene derivatives was achieved by diazotization of Et 2-amino-3-cyano-5-carbethoxythiophene-4-acetate (I) using nitrosylsulfuric acid and coupling with suitable heterocyclic hydroxy and N,N-dialkyl-substituted aryl amines. I was synthesized in one pot and in excellent yield from di-Et acetonedicarboxylate, S and malonitrile, using HNEt₂ as a catalyst, following the Gewald synthesis. The spectral properties of these dyes were studied. The dyes when applied as disperse dyes on polyester fibers gave excellent results. 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. 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).Application In Synthesis of Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate

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Synthesis of quinazolines was written by Bergman, Jan;Brynolf, Anna;Elman, Bjoern;Vuorinen, Eino. And the article was included in Tetrahedron in 1986.Electric Literature of C7H4Br2N2 This article mentions the following:

Reaction of RMgX (R = Me, Et, Ph, 4-MeC₆H₄, Me₂CH, Bu; X = Cl, Br, iodo) with 2-H₂NC₆H₄CN gave the intermediate 2-H₂NC₆H₄CR:N^– (I), which were cyclized to quinazolines by reaction with carbonyl compounds (e.g., acid chlorides, anhydrides, formates, and oxalates). Reaction of I with aldehydes, e.g. PhCHO, gave 1,2-dihydroquinazolines, which were readily dehydrogenated. Reaction of I with ClCO₂Me gave 4-phenyl-2-quinazolinone, which was reduced to 3,4-dihydro-4-phenyl-2-quinazolinone by NaBH₄ in AcOH. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5Electric Literature of C7H4Br2N2).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) 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.Electric Literature of C7H4Br2N2

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A coumarin based fluorescent chemodosimeter for phosgene gas detection instantaneously in solution and the gas phase was written by Paul, Sima;Ghosh, Pritam;Roy, Partha. And the article was included in New Journal of Chemistry in 2020.Reference of 51473-74-6 This article mentions the following:

A coumarin based compound, 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (DCCO), was developed as a visual fluorescent chemodosimeter for selective detection of highly toxic phosgene gas. DCCO exhibits absorption bands at 330 nm and 425 nm. In the presence of phosgene, the absorbance at 330 nm increases and the peak at 425 nm is shifted to 420 nm with decreasing absorbance accompanying a color change from yellow to colorless. The fluorescence intensity of the probe at 483 nm is enhanced in the presence of phosgene (λ_ex = 425 nm) but nerve agents and other acid chlorides including trisphosgene could not induce any significant enhancement of the fluorescence. DCCO on interaction with phosgene is converted to the corresponding nitrile derivative, 7-(diethylamino)-2-oxo-2H-chromene-3-carbonitrile (DCC). The quantum yield was increased 13 fold on conversion from DCCO to DCC. The fluorescence enhancement was explained by the ICT mechanism, which was supported by theor. calculations It exhibits a rapid response for naked eye detection of phosgene. DCCO was used for the detection of phosgene in solution and the gas phase. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Reference of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Reference of 51473-74-6

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Nitrile – Wikipedia,
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Reactivity of 2-aminothiophenes. Application to synthesis of thieno[2,3-b]pyrroles was written by Wierzbicki, Michel;Cagniant, Denise;Cagniant, Paul. And the article was included in Bulletin de la Societe Chimique de France in 1975.Name: Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate This article mentions the following:

Thienopyrroles I (R = H, Ac; R1 = OH, NH2; R2 = CH2CO2Et, Me; R3 = CO2Et, Ac) were prepared by treating the thiophenes II (R4 = H; R5 = CO2Et, CN) with BrCH2CO2Et and Dieckmann reaction of II (R4 = CH2CO2Et). I (R1 = OH) were alkylated with BrCH2CO2Et or acetylated. I (R2 = NH2) were acetylated and diazotized. In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Name: 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. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. 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.Name: Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

P(RNCH₂CH₂)₃N: an efficient promoter for the synthesis of 3-substituted coumarins was written by Kisanga, Philip;Fei, Xiangshu;Verkade, John. And the article was included in Synthetic Communications in 2002.Synthetic Route of C14H14N2O2 This article mentions the following:

The title compounds wherein R = Me or i-Pr function as efficient promoters for the formation of coumarins in good to excellent yields (80-95%) from salicylaldehydes and di-activated methylene compounds of the type R’CH₂CO₂Et (R’ = CO₂Et, COMe, CN). Although the yields are not generally superior to those reported in the literature, the methodol. applied here is more convenient in that milder conditions and shorter reaction times are facilitated by the use of the aforementioned com. available catalysts. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Synthetic Route of C14H14N2O2).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Synthetic Route of C14H14N2O2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

N-Alkylation of amines with alcohols over nanosized zeolite beta was written by Reddy, Marri Mahender;Kumar, Macharla Arun;Swamy, Peraka;Naresh, Mameda;Srujana, Kodumuri;Satyanarayana, Lanka;Venugopal, Akula;Narender, Nama. And the article was included in Green Chemistry in 2013.Formula: C14H12N2 This article mentions the following:

Direct N-alkylation of amines with alcs. was successfully performed by using nanosized zeolite beta, which showed the highest catalytic activity among other conventional zeolites. This method has several advantages, such as eco-friendliness, moderate to high yields, and simple work-up procedure. The catalyst was successfully recovered and reused without significant loss of activity and only water is produced as co-product. In addition, imines were also efficiently prepared from the tandem reactions of amines with 2-, 3- and 4-nitrobenzyl alcs. using nanosized zeolite beta. 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 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.Formula: C14H12N2

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ruthenium-Catalyzed Direct Reductive Amination in HCOOH/NEt₃ Mixture was written by Zhu, Mengping. And the article was included in Catalysis Letters in 2014.Reference of 10282-32-3 This article mentions the following:

Abstract: A one-pot direct reductive amination of aldehydes with primary and secondary amines using Noyori’s catalyst (η⁶-arene)Ru(H)TsDPEN in neat HCOOH/NEt₃ mixture has been developed. The catalyst formed in situ allows full conversion of aldehydes with high selectivities towards the desired amine products within hours or even minutes at room temperature For aromatic aldehydes, both 5:2 and 5:3 HCOOH/NEt₃ mixtures prove to be suitable reaction media, with the former affording higher selectivities while the latter leading to much faster reaction rates. For aliphatic aldehydes, the 5:3 HCOOH/NEt₃ mixture gives much higher selectivities due to the minimal loss from aldol condensation. This method has great application potential for the synthesis of amine products given the mild conditions. Graphical Abstract: [Figure not available: see full text.]. In the experiment, the researchers used many compounds, for example, 4-(Benzylamino)benzonitrile (cas: 10282-32-3Reference of 10282-32-3).

4-(Benzylamino)benzonitrile (cas: 10282-32-3) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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.Reference of 10282-32-3

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

A general post-synthetic modification approach of amino-tagged metal-organic frameworks to access efficient catalysts for the Knoevenagel condensation reaction was written by Luan, Yi;Qi, Yue;Gao, Hongyi;Andriamitantsoa, Radoelizo S.;Zheng, Nannan;Wang, Ge. And the article was included in Journal of Materials Chemistry A: Materials for Energy and Sustainability in 2015.Synthetic Route of C18H10N2 This article mentions the following:

Four common transition metal derived metal-organic frameworks have been extensively investigated as heterogeneous catalyst supports for Knoevenagel condensation reactions [IRMOF-3, Cr-MIL-101-NH₂, UiO-66-NH₂, and Al-MIL-53-NH₂]. A simple post-synthetic modification strategy was employed for the rapid and facile introduction of a primary alkyl amino group. The resulting novel MOF-RNH₂ catalysts showed greatly enhanced Knoevenagel condensation reactivities towards a variety of aldehyde electrophiles [R = -CH₂CH(Me)-]. IRMOF-3 proved to be an unsuitable heterogeneous catalyst support due to its fragile nature upon treatment with bases. The novel zirconium based UiO-66-NH-RNH₂ and chromium based Cr-MIL-101-NH-RNH₂ materials showed excellent catalytic reactivities, while being highly convenient to synthesize. The basic catalytic activity was further extended to the Henry reaction, and excellent catalytic reactivity was achieved. The size-selectivity was also studied to show that the Knoevenagel condensation occurred inside of the porous structure of the MOF catalyst. The recycling properties of zirconium, aluminum and chromium derived MOFs were evaluated and zirconium based UiO-66 and chromium based Cr-MIL-101 showed excellent catalytic efficiency after five reaction cycles. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Synthetic Route of C18H10N2).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Synthetic Route of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts