Tag: 200-300

Greener coumarin synthesis by Knoevenagel condensation using biodegradable choline chloride was written by Phadtare, Sunanda Balaso;Shankarling, Ganapati Subray. And the article was included in Environmental Chemistry Letters in 2012.Product Details of 51473-74-6 This article mentions the following:

Aqueous catalysis is an innovative task for the sustainable chem. industry. The use of biodegradable catalysts from natural sources may lead to greener reactions. Here, we report the synthesis of coumarin by Knoevenagel condensation using choline chloride as catalyst. Results show that even 10% of choline chloride can catalyze Knoevenagel condensation to yield coumarin in good yields. Almost all reactions proceeded faster, cleaner and in higher yields in aqueous media. Reaction mechanisms are proposed. The choline chloride catalyst was recycled five times without activity or yield decrease. Therefore, the synthesis of coumarin by Knoevenagel condensation using choline chloride as catalyst is a promising alternative to previously used procedures. In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Product Details of 51473-74-6).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. 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.Product Details of 51473-74-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Two pillared metal-organic frameworks comprising a long pillar ligand used as fluorescent sensors for nitrobenzene and heterogeneous catalysts for the Knoevenagel condensation reaction was written by Ghasempour, Hosein;Azhdari Tehrani, Alireza;Morsali, Ali;Wang, Jun;Junk, Peter C.. And the article was included in CrystEngComm in 2016.HPLC of Formula: 55490-87-4 This article mentions the following:

Two new pillared Zn and Cd-organic frameworks were synthesized by incorporating two different organic linkers, 2-aminoterephthalic acid as an O-donor linker and N4,N4′-bis(pyridin-4-ylmethylene)-biphenyl-4,4′-diamine as a long pillaring strut. The structures of these two frameworks were analyzed using x-ray crystallog., FTIR spectroscopy, thermogravimetric and elemental analyses. Their structural features as well as their stability were studied. These two MOFs having the same organic composition and the same network topol. but different inorganic nodes differ in their chem. stability. Also, these two frameworks respond differently to nitrobenzene when they were used as fluorescent sensors. Furthermore, the catalytic behavior of one of these frameworks toward the Knoevenagel condensation reaction was studied. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4HPLC of Formula: 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. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.HPLC of Formula: 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis of tetraethyl ester of 5-aminothiophene by phase transfer catalysis was written by Hu, Kai;Ding, Xiang-Yu;Jia, Xiang-Man;Jiang, Ye;Liu, Feng-Hua. And the article was included in Zhongguo Xiandai Yingyong Yaoxue in 2008.Reference of 58168-20-0 This article mentions the following:

A method for the synthesis of the title compound [i.e., tetra-Et ranelate; 5-[bis(2-ethoxy-2-oxoethyl)amino]-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid] is reported here. The synthesis of this tetra-Et ester of 5-aminothiophene was achieved by a by phase transfer catalyzed reaction and the best reaction conditions were determined Cyclization of 3-oxopentanedioic acid 1,5-di-Et ester with propanedinitrile and sulfur provided 5-amino-4-cyano-2-(ethoxycarbonyl)-3-thiopheneacetic acid Et ester. Then in acetone, tetra-Et ester of 5-aminothiophene was synthesized from 5-aminothiophene by phase transfer catalysis with Et bromoacetate in presence of a crown ether using potassium carbonate as solid base. Under optimized reaction conditions, crown ether was used as phase transfer catalyst, the molar ratio of alkylating reagent, alkali and reagent was 2.2 and 2.5 resp., the reaction temperature was 60° and the reaction time was 6 h. This method provides high product yield and purity. This is a key intermediate for strontium ranelate (a bone formation stimulant). In the experiment, the researchers used many compounds, for example, Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0Reference of 58168-20-0).

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. 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 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Function-Structure Relationship in Metal-Organic Frameworks for Mild, Green, and Fast Catalytic C-C Bond Formation was written by Razavi, Sayed Ali Akbar;Morsali, Ali. And the article was included in Inorganic Chemistry in 2019.Formula: C18H10N2 This article mentions the following:

Tunability in chem. functionality is a promising characteristic of metal-organic frameworks (MOFs), which plays an important role in developing and improving the practical applications of MOFs. Here, authors applied this important feature of MOFs to be in line with sustainable development and green chem. principles through the synthesis of MOF-based heterogeneous organocatalysts. According to their green functionalization strategy, some isostructural MOFs (azine decorated TMU-4 with the formula [Zn(OBA)(BPDB)_0.5]_n·2DMF, azine-Me functionalized TMU-5 with the formula [Zn(OBA)(BPDH)_0.5]_n·1.5DMF, dihydro-tetrazine decorated TMU-34 with the formula [Zn(OBA)(H₂DPT)_0.5]_n·DMF, and tetrazine functionalized TMU-34(-2H) with the formula [Zn(OBA)(DPT)_0.5]_n·DMF, where H₂OBA = 4,4′-oxybis(benzoic acid), BPDB = 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene, BPDH = 2,5-bis(4-pyridyl)-3,4-diaza-2,4-hexadiene, H₂DPT = 3,6-di(pyridin-4-yl)-1,4-dihydro-1,2,4,5-tetrazine, and DPT = 3,6-di(pyridin-4-yl)-1,2,4,5-tetrazine) have been applied for mild, green, and fast Knoevenagel condensation. These frameworks display different Lewis basic catalytic activities owing to their different functionality and function accessibility. Contrary to extensive articles published about Knoevenagel condensation, this study involves the rare examples in Knoevenagel condensation with such mild conditions (room temperature and atm. pressure) and with a green solution (water as the solvent). Due to the combined synergic effects of the Lewis basicity of TMU-frameworks, the amphoteric and hydrogen bond-participating nature of water mols., maximum conversion times are reached just after 30 min (for TMU-5) and 60 min (for TMU-34). Stability and recyclability tests show that TMU-5 and TMU-34 are completely stable in water at reaction conditions and can retain their crystallinity, porosity, and functionality even after five cycles without any specific reduction in their catalytic conversion. Since, in many cases, amine decorated MOFs are applied in Knoevenagel catalyzed condensation, this study is beneficial in providing information about the effects of azine and tetrazine functional groups in reactant activation and the acceleration of Knoevenagel condensation. In this work, according to green chem. principles and sustainable development, we applied some azine and tetrazine TMU-frameworks as basic heterogeneous organocatalysts for mild, green, and fast Knoevenagel condensation in water at room temperature and atm. pressure. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Formula: 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. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).Formula: C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

EPR studies of nitrogen-centered free radicals. Part 53. Isolation, EPR spectra and magnetic characterization of N-(arylthio)-2,4-diaryl-6-cyanophenylaminyls was written by Nakatsuji, Masaaki;Miura, Yozo;Teki, Yoshio. And the article was included in Journal of the Chemical Society, Perkin Transactions 2 in 2001.SDS of cas: 68385-95-5 This article mentions the following:

N-(Arylthio)-2,4-diaryl-6-ethoxycarbonylphenylaminyls (1), N-[(2,4-dichlorophenyl)thio]-2,4-diphenyl-6-acetyl-phenylaminyl (2), N-(arylthio)-2,4-diaryl-6-cyanophenylaminyls (3), N-[(2,4-dichlorophenyl)thio]-2,4-bis(4-chloro-phenyl)-6-fluorophenylaminyl (4) and N-[(4-nitrophenyl)thio]-2,4-diphenylphenylaminyl (5) were generated by oxidation of the corresponding N-(arylthio)anilines. Although 4 and 5 were short-lived and decayed in 30 min, 1-3 were quite persistent and 3 could be isolated as radical crystals. EPR spectra were measured for all radicals generated and the spin d. distribution was evaluated. Ab initio MO calculations (the UHF Becke 3LYP/STO 6-31G) were performed, and a quant. discussion on the spin d. distribution was made. Magnetic susceptibility measurements were performed for three isolated radicals with a SQUID magnetometer. One radical was found to couple ferromagnetically, and anal. with the one-dimensional regular Heisenberg model gave 2J/k_B = 11.2 K. In the experiment, the researchers used many compounds, for example, 2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5SDS of cas: 68385-95-5).

2-Amino-3,5-dibromobenzonitrile (cas: 68385-95-5) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. In addition, Nitriles can react with alkynes, which leads to an increase in carbon chain length (carbocyanation).SDS of cas: 68385-95-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Antihypertensive activity of 6-arylpyrido[2,3-d]pyrimidin-7-amine derivatives was written by Bennett, Lawrence R.;Blankley, C. John;Fleming, Robert W.;Smith, Ronald D.;Tessman, Deirdre K.. And the article was included in Journal of Medicinal Chemistry in 1981.COA of Formula: C8H5Br2N This article mentions the following:

Fifty-one title compounds I (R = H, Me, Et, etc.; R¹ = H, Me, OEt, etc.; R² = substituted phenyl) were synthesized and evaluated for antihypertensive activity in the conscious spontaneously hypertensive rat. A number of these compounds, notably 6-(2,6-dichlorophenyl)-2-methylpyrido[2,3-d]pyrimidin-7-amine [76574-80-6], lowered blood pressure in these rats in a gradual and sustained manner to normotensive levels at oral doses of 10-50 mg/kg. Normalized blood pressure levels could then be maintained by single daily oral doses. The effect of structural variation in the 6-aryl group and in the 2 and 4 positions of the pyridopyrimidine ring on activity is reported and discussed. In the experiment, the researchers used many compounds, for example, 2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9COA of Formula: C8H5Br2N).

2-(2,6-Dibromophenyl)acetonitrile (cas: 67197-53-9) 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.COA of Formula: C8H5Br2N

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Zinc-proline complex catalyzed Knoevenagel condensation in water was written by Yan, Shiqiang;Guo, Wei;Wang, Wensheng;Zhang, Wei. And the article was included in Youji Huaxue in 2019.Computed Properties of C18H10N2 This article mentions the following:

Zinc-proline complex catalyzed Knoevenagel condensation in water was reported. Seventeen aldehydes and two ketones were investigated, which coupled with malononitrile smoothly affording desired Knoevenagel condensation products in 5∼10 min at 80°C in the yields of 84%∼99%. The catalyst can be recovered and reused for ten cycles without loss of activity. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Computed Properties of C18H10N2).

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. 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.Computed Properties of C18H10N2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target Burkitt’s lymphoma was written by Byrne, Andrew J.;Bright, Sandra A.;McKeown, James P.;O’Brien, John E.;Twamley, Brendan;Fayne, Darren;Clive Williams, D.;Meegan, Mary J.. And the article was included in Pharmaceuticals in 2020.Product Details of 55490-87-4 This article mentions the following:

The synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds such as I [R¹ = H, Cl; R² = H, Me, Et; X = O, NH, N(C₆H₅), etc.], II and III [R³ = CN, CO₂Me, CO₂Et, OC(O)Me; R⁴ = H, CN; R⁵ = H, CO₂Me, CO₂Et] structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG-75 was reported. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2-nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds I [R¹ = Cl, R² = H, X = NH, N(C₆H₅); R¹ = R² = H, X = N(C₆H₅), N(4-ClC₆H₄), N(4-OMeC₆H₄)], II and III [R³ = CN, R⁴ = R⁵ = H] displayed IC₅₀ values in the range 0.17-0.38μM against the BL cell line EBV- MUTU-1 and IC50 values in the range 0.45-0.78μM against the chemoresistant BL cell line EBV+ DG-75. Compounds I [R¹ = R² = H, X = N(4-ClC₆H₄), N(4-OMeC₆H₄)] and II demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells. The results suggested that this class of compounds merits further investigation as antiproliferative agents for BL. In the experiment, the researchers used many compounds, for example, 2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4Product Details of 55490-87-4).

2-(Anthracen-9-ylmethylene)malononitrile (cas: 55490-87-4) 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. Industrially, the main methods for producing nitriles are ammoxidation and hydrocyanation. Both routes are green in the sense that they do not generate stoichiometric amounts of salts.Product Details of 55490-87-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Ketene gem-dithiols; a convenient one-step procedure from aliphatic active methylenes: reactions and synthesis of polyfunctionally substituted thia- and azaheteroaromatics was written by Zayed, Salem E.. And the article was included in Phosphorus, Sulfur and Silicon and the Related Elements in 1996.Application of 58168-20-0 This article mentions the following:

It has been reported in the current literature that the isolation of certain ketene gem dithiols has failed due to dimerization. Generation of ketene gem-dithiols via trapping with other reactants led to formation of pyridine, pyrrole, pyridothiadiazole and pyrazolone derivatives 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 of 58168-20-0).

Ethyl 5-amino-4-cyano-3-(2-ethoxy-2-oxoethyl)thiophene-2-carboxylate (cas: 58168-20-0) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Application of 58168-20-0

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reaction of 4-(diethylamino)salicylaldehyde with malononitrile was written by Tkach, I. I.;Reznichenko, A. V.;Luk’yanets, E. A.. And the article was included in Khimiya Geterotsiklicheskikh Soedinenii in 1992.Name: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile This article mentions the following:

Treating 4-(diethylamino)salicylaldehyde (I) with CH₂(CN)₂ in AcOH gave 27% coumarin derivative II and 6.2% coumarin III; in polyphosphoric acid 53% amide IV was obtained; and in Ac₂O 49% dicyanovinyl derivative V was obtained. Addnl. obtained were thione VI and benzopyranonaphthyridines VII (R = H, Et). In the experiment, the researchers used many compounds, for example, 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6Name: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile).

7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile (cas: 51473-74-6) 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. 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: 7-(Diethylamino)-2-oxo-2H-chromene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts