Tag: 100-200

Synthesis and Characterization of Amidato Divalent Lanthanide Complexes and Their Use in Forming 2,4-Quinazolidinones from CO₂ and 2-Aminobenzonitriles was written by Wang, Qianyu;Lu, Chengrong;Zhao, Bei;Yao, Yingming. And the article was included in European Journal of Organic Chemistry in 2016.Application In Synthesis of 2-Amino-3-chlorobenzonitrile This article mentions the following:

Four amidato divalent lanthanide complexes, {LⁿLn[N(TMS)₂]THF}₂ [n = 1, Ln = Eu (I); n = 2, Ln = Eu (III), Yb (IV); HL¹ = tBuC₆H₄CONHC₆H₃(iPr)₂; HL² = C₆H₅CONHC₆H₃(iPr)₂] and {L³Eu[N(TMS)₂]THF}{L³₂Eu(THF)₂} (II) [HL³ = ClC₆H₄CONHC₆H₃(iPr)₂], were synthesized and extensively characterized. This is the first time that the amidato lanthanide amides I–IV were used to catalyze the reactions of CO₂ and 2-aminobenzonitriles to form quinazoline-2,4(1H,3H)-diones at atm. pressure. All the complexes efficiently catalyzed the transformation, with complex III showing the highest activity. This catalytic system gave good to excellent yields, and good functional group tolerance. Preliminary studies were conducted to investigate the reaction mechanism. In the experiment, the researchers used many compounds, for example, 2-Amino-3-chlorobenzonitrile (cas: 53312-77-9Application In Synthesis of 2-Amino-3-chlorobenzonitrile).

2-Amino-3-chlorobenzonitrile (cas: 53312-77-9) 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. 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.Application In Synthesis of 2-Amino-3-chlorobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pyridinylpyrimidines selectively inhibit human methionine aminopeptidase-1 was written by Zhang, Pengtao;Yang, Xinye;Zhang, Feiran;Gabelli, Sandra B.;Wang, Renxiao;Zhang, Yihua;Bhat, Shridhar;Chen, Xiaochun;Furlani, Manuel;Amzel, L. Mario;Liu, Jun O.;Ma, Dawei. And the article was included in Bioorganic & Medicinal Chemistry in 2013.Recommanded Product: 4-methoxypicolinonitrile This article mentions the following:

Cellular protein synthesis is initiated with methionine in eukaryotes with few exceptions. Methionine aminopeptidases (MetAPs) which catalyze the process of N-terminal methionine excision are essential for all organisms. In mammals, type 2 MetAP (MetAP2) is known to be important for angiogenesis, while type 1 MetAP (MetAP1) has been shown to play a pivotal role in cell proliferation. Authors’ previous high-throughput screening of a com. compound library uncovered a novel class of inhibitors for both human MetAP1 (HsMetAP1) and human MetAP2 (HsMetAP2). This class of inhibitors contains a pyridinylpyrimidine core. To understand the structure-activity relationship (SAR) and to search for analogs of 2 with greater potency and higher HsMetAP1-selectivity, a total of 58 analogs were acquired through either com. source or by inhouse synthesis and their inhibitory activities against HsMetAP1 and HsMetAP2 were determined Through this systematic medicinal chem. anal., the authors have identified: (1) 5-chloro-6-methyl-2-pyridin-2-ylpyrimidine as the min. element for the inhibition of HsMetAP1; (2) 5′-chloro as the favored substituent on the pyridine ring for the enhanced potency against HsMetAP1; and (3) long C4 side chains as the essentials for higher HsMetAP1-selectivity. As a result of the SAR campaign, six compounds were found to be among the most selective and potent inhibitors of purified HsMetAP1 reported to date. In addition, crystallog. anal. of one representative inhibitor (I) in complex with N-terminally truncated HsMetAP1 was also performed. Map gene. In the experiment, the researchers used many compounds, for example, 4-methoxypicolinonitrile (cas: 36057-44-0Recommanded Product: 4-methoxypicolinonitrile).

4-methoxypicolinonitrile (cas: 36057-44-0) 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 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.Recommanded Product: 4-methoxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Immobilization of chiral Rh catalyst on glass and application to asymmetric transfer hydrogenation of aryl ketones in aqueous media was written by Cheng, Tan-Yu;Zhuang, Jing-Lan;Yao, Hui;Zhang, Huai-Sheng;Liu, Guo-Hua. And the article was included in Chinese Chemical Letters in 2014.Reference of 101219-69-6 This article mentions the following:

A chiral catalyst, Cp^*RhTsDPEN (Cp^* = pentamethylcyclopentadiene, TsDPEN = substituted N-phenylsulfonyl-1,2-diphenylethylenediamine), was synthesized and immobilized at the surface of glass. The immobilized catalyst exhibited good catalytic efficiency for asym. transfer hydrogenation of aromatic ketones in water with HCO₂Na as hydrogen source. In the experiment, the researchers used many compounds, for example, (R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6Reference of 101219-69-6).

(R)-4-(1-Hydroxyethyl)benzonitrile (cas: 101219-69-6) 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. 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. Reference of 101219-69-6

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Rates and equilibriums for the interaction of cyanonitrothiophene derivatives with the methoxide ion in methanol solution was written by Doddi, Giancarlo;Illuminati, Gabriello;Stegel, Franco. And the article was included in Tetrahedron Letters in 1973.Recommanded Product: 4-Nitrothiophene-2-carbonitrile This article mentions the following:

Addition of MeO- to 4-cyano-2-nitrothiophene and 2,4-dinitrothiophene, in MeOH solution gave Meisenheimer adducts of type (I, R = CN, NO2). However, 2-cyano-4-nitrothiophene gave Me 4-nitro-2-thiophenecarboximidate, the Meisenheimer adduct being formed on solution of the solid in Me2SO. Normal Meisenheimer adducts with MeO- in MeO-H solution were formed by 2-cyano-5-methoxy-4-nitrothiophene and the 2,4-dinitro analog. Kinetic and equilibrium constants for the adduct formation were determined by visible and NMR spectroscopy. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Recommanded Product: 4-Nitrothiophene-2-carbonitrile).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. Trimerization of aromatic nitriles requires harsh reaction conditions, high temperatures, long reaction times, and pressure. 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.Recommanded Product: 4-Nitrothiophene-2-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis and SAR study of potent and selective PI3Kδ inhibitors was written by Bui, Minna;Hao, Xiaolin;Shin, Youngsook;Cardozo, Mario;He, Xiao;Henne, Kirk;Suchomel, Julia;McCarter, John;McGee, Lawrence R.;San Miguel, Tisha;Medina, Julio C.;Mohn, Deanna;Tran, Thuy;Wannberg, Sharon;Wong, Jamie;Wong, Simon;Zalameda, Leeanne;Metz, Daniela;Cushing, Timothy D.. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2015.Quality Control of 4-Amino-6-chloropyrimidine-5-carbonitrile This article mentions the following:

2,3,4-Substituted-quinolines such as I were found to be potent inhibitors of PI3Kδ in both biochem. and cellular assays with good selectivity over three other class I PI3K isoforms. Some of those analogs showed favorable pharmacokinetic properties. In the experiment, the researchers used many compounds, for example, 4-Amino-6-chloropyrimidine-5-carbonitrile (cas: 60025-09-4Quality Control of 4-Amino-6-chloropyrimidine-5-carbonitrile).

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. 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. Quality Control of 4-Amino-6-chloropyrimidine-5-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Facile Synthesis of 2-Aminothiophenes Using NaAlO₂ as an Eco-Effective and Recyclable Catalyst was written by Bai, Rongxian;Liu, Ping;Yang, Jian;Liu, Changhui;Gu, Yanlong. And the article was included in ACS Sustainable Chemistry & Engineering in 2015.Product Details of 70291-62-2 This article mentions the following:

Substituted 2-aminothiophenes were synthesized through Gewald reaction by using an easily available solid base catalyst, sodium aluminate. Cost-effectiveness, mild and environmentally benign conditions, and excellent catalytic performance are the features of this system. Furthermore, the NaAlO₂ catalyst can be swimmingly recovered and reused in this reaction. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Product Details of 70291-62-2).

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. 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 70291-62-2

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Discovery, Optimization, and Biological Evaluation of 5-(2-(Trifluoromethyl)phenyl)indazoles as a Novel Class of Transient Receptor Potential A1 (TRPA1) Antagonists was written by Rooney, Lisa;Vidal, Agnes;D’Souza, Anne-Marie;Devereux, Nick;Masick, Brian;Boissel, Valerie;West, Ryan;Head, Victoria;Stringer, Rowan;Lao, Jianmin;Petrus, Matt J.;Patapoutian, Ardem;Nash, Mark;Stoakley, Natalie;Panesar, Moh;Verkuyl, J. Martin;Schumacher, Andrew M.;Petrassi, H. Michael;Tully, David C.. And the article was included in Journal of Medicinal Chemistry in 2014.Category: nitriles-buliding-blocks This article mentions the following:

A high throughput screening campaign identified 5-(2-chlorophenyl)indazole as an antagonist of the transient receptor potential A1 (TRPA1) ion channel with IC₅₀ = 1.23 μM. Hit to lead medicinal chem. optimization established the SAR around the indazole ring system, demonstrating that a trifluoromethyl group at the 2-position of the Ph ring in combination with various substituents at the 6-position of the indazole ring greatly contributed to improvements in vitro activity. Further lead optimization resulted in the identification of compound I, a potent and selective antagonist of TRPA1 in vitro (IC₅₀ = 0.015 μM), which has moderate oral bioavailability in rodents and demonstrates robust activity in vivo in several rodent models of inflammatory pain. In the experiment, the researchers used many compounds, for example, 3-Amino-4-methylbenzonitrile (cas: 60710-80-7Category: nitriles-buliding-blocks).

3-Amino-4-methylbenzonitrile (cas: 60710-80-7) 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.Category: nitriles-buliding-blocks

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

An efficient one-pot synthesis of substituted 2-aminothiophenes via three-component Gewald reaction catalyzed by L-proline was written by Wang, Tao;Huang, Xian-Gui;Liu, Jia;Li, Bo;Wu, Jin-Jin;Chen, Kai-Xian;Zhu, Wei-Liang;Xu, Xiao-Yong;Zeng, Bu-Bing. And the article was included in Synlett in 2010.Synthetic Route of C8H8N2S This article mentions the following:

An efficient one-pot procedure for the direct catalytic synthesis of substituted 2-aminothiophenes catalyzed by L-proline under mild reaction conditions was developed. A variety of functionalized 2-aminothiophene scaffolds were assembled in high yields by this catalytic protocol. Low catalyst loading, simple procedure, and high yields are the important attributes of this methodol. In the experiment, the researchers used many compounds, for example, 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2Synthetic Route of C8H8N2S).

2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile (cas: 70291-62-2) 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. 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 C8H8N2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthesis, crystal structures and biological activity of two enantiomeric 2-trifluoromethylthieno[2,3-d]pyrimidin-4-amine derivatives was written by Gao, Hui;Fu, Ju;Zhao, Ming-juan;Song, Xin-jian;Yang, Ping;Zheng, Yin. And the article was included in Chinese Journal of Structural Chemistry in 2015.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile This article mentions the following:

Two enantiomeric 2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine derivatives were synthesized by nucleophilic substitution of two chiral amines with 4-chloro-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidine, which started from 2-amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile, trifluoroacetic acid (TFA) and phosphoryl trichloride via one-pot procedure [I → II; II + (R)/(S)-α-methylbenzylamine → (R)/(S)-III]. Their structures were determined by single-crystal X-ray diffraction. Enantiomer (R)-III, (R)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system, space group P4₃ with a = 8.6847(6), b = 8.6847(6), c = 22.419(2) Å, V = 1690.9(3) ų, Z = 4, D_c = 1.428 g/cm³, μ = 0.228 mm^-1, F(000) = 752, the final R = 0.0463 and wR = 0.1257 for 3442 observed reflections with I > 2(I). Enantiomer (S)-III, (S)-N-(1-phenylethyl)-2-trifluoromethyl-6,7-dihydro-5H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-amine crystallizes in the tetragonal system, space group P41 with a = 8.688, b = 8.688, c = 22.421 Å, V = 1692.4 ų, Z = 4, Dc = 1.426 g/cm³, μ = 0.227 mm^-1, F(000) = 752, the final R = 0.0682 and wR = 0.1806 for 3182 observed reflections with I > 2(I). The preliminary bioassay indicated that the R-enantiomer exhibits higher antitumor activity against MCF-7 than gefitinib. 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. 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.Recommanded Product: 2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophene-3-carbonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Conversions of carbonyl compounds via their polymeric sulfonylhydrazones into alkenes, alkanes, and nitriles was written by Kamogawa, Hiroyoshi;Kanzawa, Asami;Kadoya, Masahiro;Naito, Takeshi;Nanasawa, Masato. And the article was included in Bulletin of the Chemical Society of Japan in 1983.Name: 2-Cyclohexylacetonitrile This article mentions the following:

RR¹CO [R = H, R¹ = (CH₂)₅Me, Ph, cyclohexyl; R = Me, R¹ = Ph, CH₂CH₂Ph; R = R¹ = Ph, CH₂Ph; RR¹ = (CH₂)₅, (CH₂)₁₁, (CH₂)₂CHMe; RR¹CO = camphor] reacted with hydrazine bound to sulfonated styrene-divinylbenzene copolymer to form polymer-bound sulfonylhydrazones (I). I reacted with alkali to give alkenes, with NaBH₄ or LiAlH₄ to give RCH_iR¹, and with KCN to give RR¹CHCN. The extent of the reaction depended on the type of resin and the bulk of RR¹CO. In the experiment, the researchers used many compounds, for example, 2-Cyclohexylacetonitrile (cas: 4435-14-7Name: 2-Cyclohexylacetonitrile).

2-Cyclohexylacetonitrile (cas: 4435-14-7) 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.Name: 2-Cyclohexylacetonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts