Month: January 2023

Activation of elemental sulfur by electrogenerated cyanomethyl anion: synthesis of substituted 2-aminothiophenes by the Gewald reaction was written by Feroci, Marta;Chiarotto, Isabella;Rossi, Leucio;Inesi, Achille. And the article was included in Advanced Synthesis & Catalysis in 2008.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

The activation of elemental sulfur (S₈) has been achieved using the electrogenerated cyanomethyl anion [easily obtained by galvanostatic reduction from acetonitrile/tetraethylammonium hexafluorophosphate (MeCN-Et₄NPF₆)]. The “activated” sulfur reacted with ylidenemalononitriles to give substituted 2-aminothiophenes in very high yields. This variation of the Gewald reaction has been carried out using only catalytic amounts of electricity and supporting electrolyte. A proposed mechanism for the interaction between S₈ and cyanomethyl anion is described. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Recommanded Product: 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. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and antiallergy activity of [1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one derivatives. II. 6-Alkyl- and 6-cycloalkylalkyl derivatives was written by Yokohama, Shuichi;Miwa, Tamotsu;Aibara, Shunzo;Fujiwara, Hiroyuki;Matsumoto, Hiroo;Nakayama, Kiyoshi;Iwamoto, Teiji;Mori, Mikio;Moroi, Reimei. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.Application In Synthesis of 2-Cyclohexylacetonitrile This article mentions the following:

A series of 6-alkyl- or 6-(cycloalkylalkyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-ones, including I (R = cyclopentylethyl, cyclopentylpropyl, cyclohexylmethyl, cyclohexylpropyl, cycloheptylethyl, cyclooctylethyl, cyclododecylethyl), was synthesized from the corresponding 1,3,4-thiadiazol-5-amines II and the antiallergic activities of the products were evaluated. Among these compounds 6-(2-cyclohexylethyl)-[1,3,4]thiadiazolo[3,2-a]-1,2,3-triazolo[4,5-d]pyrimidin-9(3H)-one (I, R = cyclohexylethyl), whose x-ray crystallog. stereostructure was determined, is a promising new antiallergic agent, which has low toxicity and dual activity as a leukotriene D₄ receptor antagonist and as an orally active mast cell stabilizer. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Application In Synthesis of 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitriles are polar, as indicated by high dipole moments. As liquids, they have high relative permittivities, often in the 30s. 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.Application In Synthesis of 2-Cyclohexylacetonitrile

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

A facile microwave assisted synthesis and anti-inflammatory activity of thiophene[3,2- e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one derivatives was written by Kaur, Rajwinder;Rao, Akkinepally Raghuram;Chadha, Renu;Thakur, Nishant;Goswami, Manish. And the article was included in International Journal of Pharmaceutical Sciences Review and Research in 2016.Category: nitriles-buliding-blocks This article mentions the following:

A series of novel substituted triazolo thieno pyrimidines (5-12) was synthesized by employing innovative synthetic methods. Two methods (A and B) were employed for the synthesis of compounds 3-12. Method B (microwave assisted) was found to be facile, economic and less time consuming compared to conventional method (method A) adopted. The microwave irradiation provided an environment-friendly, remarkable rate of acceleration for the reaction with reduced reaction time and in some cases (under MW irradiation) the yields are also substantially higher. Anti-inflammatory activity and mast cell degranulation studies of synthesized compounds were carried out. Indomethacin was taken as a reference standard in carrageenan induced rat paw edema model for anti-inflammatory studies and in mast cell degranulation studies disodium cromoglycate was used for comparison. All compounds showed a good anti-inflammatory response and mast cell stabilization. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Category: nitriles-buliding-blocks).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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 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.Category: nitriles-buliding-blocks

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

Highly recoverable organoruthenium-functionalized mesoporous silica boosts aqueous asymmetric transfer hydrogenation reaction was written by Liu, Rui;Cheng, Tanyu;Kong, Lingyu;Chen, Chen;Liu, Guohua;Li, Hexing. And the article was included in Journal of Catalysis in 2013.Synthetic Route of C9H9NO This article mentions the following:

Exploring functionalized mesoporous silica to achieve enhanced catalytic activity and enantioselectivity in heterogeneous asym. catalysis presents a significant challenge that is critical for understanding the function of support and controlling chiral complexation behavior. In this contribution, by cooperative assembly of chiral 4-((trimethoxysilyl)ethyl)phenylsulfonyl-1,2-diphenylethylene-diamine and tetraethoxysilane followed by complexation with organoruthenium complex, we report a unique three-dimensional chiral organoruthenium-functionalized chrysanthemum-like mesoporous silica (CMS). As demonstrated in the studies, taking advantage of the active site-isolated chiral organoruthenium catalytic nature, this heterogeneous catalyst ArRuTsDPEN-CMS (Ar = hexamethylbenzene, TsDPEN = 4-methylphenylsulfonyl-1,2-diphenylethylene-diamine) displays enhanced catalytic activity and enantioselectivity in aqueous asym. transfer hydrogenation with extensive substrates. Furthermore, this heterogeneous catalyst can be conveniently recovered and reused at least 10 times without loss of its catalytic efficiency. These features render this catalyst particularly attractive in practice of organic synthesis in an environmentally friendly manner. Also, this outcome from the study clearly shows that the strategy described here offers a general approach to immobilization of chiral ligand-derived silane onto a functionalized mesoporous material with significant improving catalytic activity. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Synthetic Route of C9H9NO).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 C9H9NO

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Hydrogenation of alkenes over nickel nanoparticles under atmospheric pressure of hydrogen was written by Mokhov, V. M.;Popov, Yu. V.;Nebykov, D. N.. And the article was included in Russian Journal of Organic Chemistry in 2016.Reference of 4435-14-7 This article mentions the following:

Nickel nanoparticles are an accessible catalyst which allows hydrogenation of unsaturated compounds to be accomplished under atm. pressure of hydrogen at relatively low temperatures Linear and cyclic alkenes, styrene and norbornene derivatives, as well as pinenes and camphene were smoothly hydrogenated under these conditions. In some cases, selective hydrogenation of unsaturated carbon-carbon bond is possible with the other functional group remaining intact. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Reference of 4435-14-7).

2-Cyclohexylacetonitrile (cas: 4435-14-7) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. 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 4435-14-7

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

Development of Inhibitors of SAICAR Synthetase (PurC) from Mycobacterium abscessus Using a Fragment-Based Approach was written by Charoensutthivarakul, Sitthivut;Thomas, Sherine E.;Curran, Amy;Brown, Karen P.;Belardinelli, Juan M.;Whitehouse, Andrew J.;Acebron-Garcia-de-Eulate, Marta;Sangan, Jaspar;Gramani, Subramanian G.;Jackson, Mary;Mendes, Vitor;Floto, R. Andres;Blundell, Tom L.;Coyne, Anthony G.;Abell, Chris. And the article was included in ACS Infectious Diseases in 2022.Recommanded Product: 60025-09-4 This article mentions the following:

In this study, SAICAR synthetase (PurC) from Mab was identified as a promising target for novel antibiotics. An inhouse fragment library screen and a high-throughput X-ray crystallog. screen of diverse fragment libraries were explored to provide crucial starting points for fragment elaboration. A series of compounds developed from fragment growing and merging strategies, guided by crystallog. information and careful hit-to-lead optimization, have achieved potent nanomolar binding affinity against the enzyme. Some compounds also show a promising inhibitory effect against Mab and Mtb. This work utilizes a fragment-based design and demonstrates for the first time the potential to develop inhibitors against PurC from Mab. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Recommanded Product: 60025-09-4).

4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4) belongs to nitriles. Nitrile carbon shifts are in the range of 115–125 ppm whereas in isonitriles the shifts are around 155–165 ppm. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Recommanded Product: 60025-09-4

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Triazoloquinazolines as a novel class of phosphodiesterase 10A (PDE10A) inhibitors was written by Kehler, Jan;Ritzen, Andreas;Langgard, Morten;Petersen, Sebastian Leth;Farah, Mohamed M.;Bundgaard, Christoffer;Christoffersen, Claus Tornby;Nielsen, Jacob;Kilburn, John Paul. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2011.Category: nitriles-buliding-blocks This article mentions the following:

Novel triazoloquinazolines have been found as phosphodiesterase 10A (PDE10A) inhibitors. Structure-activity studies improved the initial micromolar potency which was found in the lead compound by a 100-fold identifying 5-(1H-benzoimidazol-2-ylmethylsulfanyl)-2-methyl-[1,2,4]triazolo[1,5-c]quinazoline, 42 (PDE10A IC₅₀ = 12 nM) as the most potent compound from the series. Two X-ray structures revealed novel binding modes to the catalytic site of the PDE10A enzyme. In the experiment, the researchers used many compounds, for example, 2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1Category: nitriles-buliding-blocks).

2-Amino-4-(trifluoromethyl)benzonitrile (cas: 1483-54-1) 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. 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.Category: nitriles-buliding-blocks

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts