Category: amides-buliding-blocks

Efficient and general one-pot synthesis of β-chloro-β-trifluoromethylated enones from 3,3,3-trifluoropropyne was written by Jeon, Sung Lan;Kim, Dae Ho;Son, Jang Bae;Jeong, In Howa. And the article was included in Bulletin of the Korean Chemical Society in 2006.Safety of 4-Bromo-N-methoxy-N-methylbenzamide This article mentions the following:

CF₃CCH reacted with Weinreb amides in BuLi/THF to give CF₃CCl:CHCOR [R = (un)substituted Ph, 1-naphthalenyl, 2-furanyl, cyclohexyl] as E-Z mixtures In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Safety of 4-Bromo-N-methoxy-N-methylbenzamide).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Safety of 4-Bromo-N-methoxy-N-methylbenzamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Enantioselective synthesis of dihydropyrans. Catalysis of hetero Diels-Alder reactions by bis(oxazoline) copper(II) complexes was written by Evans, David A.;Johnson, Jeffrey S.;Olhava, Edward J.. And the article was included in Journal of the American Chemical Society in 2000.Synthetic Route of C6H12N2O4 This article mentions the following:

C₂-sym. bis(oxazoline)-Cu(II) complexes catalyze the inverse electron demand hetero Diels-Alder reaction of α,β-unsaturated carbonyl compounds (heterodiene), e.g., (MeO)₂P(O)COCR¹:CR²R³ (R¹, R³ = H, Me, R² = Me, Ph, CHMe₂, EtO, Et), with electron-rich olefins (heterodienophile), e.g., EtOCH:CH₂, in high diastereo- and enantioselectivity. α,β-Unsaturated acyl phosphonates and β,γ-unsaturated α-keto esters and amides are effective heterodienes, while enol ethers and sulfides function as heterodienophiles. A range of substitution patterns is possible on the heterodiene: terminal alkyl, aryl, alkoxy, and thioether substituents are all tolerated. The enantioselective synthesis of dihydropyrans such as I by this method has been shown to be straightforward: cycloadditions may be conducted with as little as 0.2 mol % of the chiral catalyst and are readily run on multigram scale. The reactions exhibit a favorable temperature-enantioselectivity profile, with selectivities exceeding 90% even at room temperature A simple reaction protocol that employs a solid air-stable catalyst, convenient reaction temperatures, and low catalyst loadings is described. The utility of the derived cycloadducts in the preparation of chiral building blocks is demonstrated. Models for asym. induction are discussed considering product stereochem., X-ray crystallog. data for the solid catalysts, and mechanistic studies. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Synthetic Route of C6H12N2O4).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) belongs to amides. Amides are pervasive in nature and technology. Proteins and important plastics like Nylons, Aramid, Twaron, and Kevlar are polymers whose units are connected by amide groups (polyamides); these linkages are easily formed, confer structural rigidity, and resist hydrolysis. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Synthetic Route of C6H12N2O4

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Screening of 484 trace organic contaminants in coastal waters around the Liaodong Peninsula, China: Occurrence, distribution, and ecological risk was written by Xie, Huaijun;Chen, Jingwen;Huang, Yang;Zhang, Ruohan;Chen, Chang-Er;Li, Xuehua;Kadokami, Kiwao. And the article was included in Environmental Pollution (Oxford, United Kingdom) in 2020.Recommanded Product: 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid This article mentions the following:

Human activities such as agriculture, aquaculture, and industry can lead to the pollution of coastal waters by trace organic contaminants (TrOCs), and the TrOCs can pose a threat to marine ecosystems. Therefore, it is essential to investigate the occurrence, distribution, and ecol. risk of the TrOCs in coastal waters. Previous studies adopting conventional anal. methods have focused on a limited number of targets. Herein, a comprehensive and systematic determination was undertaken to target 484 TrOCs in the waters around the Liaodong Peninsula, China. Eighty-six TrOCs were detected at concentrations of up to 350 ng L-1, and 25 TrOCs were detected at a frequency of >50%. Pesticides were the predominant pollutants, occurring at high concentrations with large detection frequencies. Ecol. risks were assessed for single pollutants and mixtures based on the risk quotient and concentration addition modeling, resp. The detected pesticides posed relatively high risk to aquatic organisms, while pharmaceuticals, consumer products, and other pollutants posed little or no risk. TrOC mixtures posed extremely high risk to aquatic organisms, which represented a significant threat to the marine environment and local communities. The results described here provide useful information that can inform China’s “Action Plan for Prevention and Control of Water Pollution”. In the experiment, the researchers used many compounds, for example, 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8Recommanded Product: 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid).

2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid (cas: 53902-12-8) belongs to amides. Amides can be viewed as a derivative of a carboxylic acid RC(=O)OH with the hydroxyl group –OH replaced by an amine group −NR′R″; or, equivalently, an acyl (alkanoyl) group RC(=O)− joined to an amine group. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Recommanded Product: 2-(3-(3,4-Dimethoxyphenyl)acrylamido)benzoic acid

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

An Efficient Approach to Azolyl-Substituted Steroids through Copper-Catalyzed Ullmann C-N Coupling was written by Kotovshchikov, Yury N.;Latyshev, Gennadij V.;Lukashev, Nikolay V.;Beletskaya, Irina P.. And the article was included in European Journal of Organic Chemistry in 2013.Computed Properties of C11H15NO2 This article mentions the following:

Ullmann-type C-N coupling of vinyliodides and nitrogen heterocycles has been shown to be a straightforward and highly efficient approach to azolyl-substituted steroids, e.g., I [R = H, OMe, Br] and II. The amination reaction proved sensitive to steric effects exerted by the substituents in both iodide and heterocycle. The influence of reaction conditions (catalyst, base, solvent, and temperature) on conversion of the iodosteroid and the selectivity was investigated. The catalytic system comprising 10 mol-% CuI and 20 mol-% dipivaloylmethane with K₂CO₃ in DMSO at 100 °C delivered the best result. The elaborated protocol has permitted iodosteroids with various substituted indoles, imidazoles, carbazole, indazole, and sec-amides to be coupled, affording the corresponding azolyl-substituted steroids in good to excellent yields. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Computed Properties of C11H15NO2).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides are stable compounds. The lower-melting members (such as acetamide) can be readily purified by fractional distillation. Most amides are solids which have low solubilities in water.Computed Properties of C11H15NO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

A substituent- and temperature-controllable NHC-derived zwitterionic catalyst enables CO₂ upgrading for high-efficiency construction of formamides and benzimidazoles was written by Yu, Zhaozhuo;Li, Zhengyi;Zhang, Lilong;Zhu, Kaixun;Wu, Hongguo;Li, Hu;Yang, Song. And the article was included in Green Chemistry in 2021.Recommanded Product: N-Cyclopropylformamide This article mentions the following:

Chemocatalytic upgrading of the greenhouse gas CO₂ to valuable chems. and biofuels has attracted broad attention in recent years. Among the reported approaches, N-formylation of CO₂ with an amine is of great significance due to its versatility in the construction of N-containing linear and cyclic skeletons. Herein, a stable N-heterocyclic carbene-carboxyl adduct (NHC-CO₂) was facilely prepared and could be used as a recyclable zwitterionic catalyst for efficient CO₂ reductive upgrading via either N-formylation or further coupling with cyclization under mild conditions (25°C, 1 atm CO₂) using hydrosilane as a hydrogen source. More than 30 different alkyl and aromatic amines could be transformed into the corresponding formamides or benzimidazoles with remarkable yields (74%-98%). The electronic effect of the introduced substituent on NHC-CO₂ was found to evidently affect the thermostability and nucleophilicity of the zwitterionic catalyst, which is directly correlated with its catalytic activity. Moreover, NHC-CO₂ could supply CO₂ by in situ decarboxylation at a specific temperature that is dependent on the introduced substituent type. Exptl. and computational studies showed that the carboxyl species on NHC-CO₂ was not only a nucleophilic center, but also a C1 source which rapidly captures or substitutes ambient CO₂ during hydrosilylation. In addition, a simple and green conceptual process was designed for the product purification and catalyst recycling, with a good feasibility for small-scale production In the experiment, the researchers used many compounds, for example, N-Cyclopropylformamide (cas: 58644-54-5Recommanded Product: N-Cyclopropylformamide).

N-Cyclopropylformamide (cas: 58644-54-5) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides can be freed from solvent or water by drying below their melting points. These purifications can also be used for sulfonamides and acid hydrazides.Recommanded Product: N-Cyclopropylformamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Pharmacological research on new salicylic and gentisic acid derivatives. III. Influences on pressure and respiration was written by Preziosi, P.;Reduzzi, F.. And the article was included in Archivio Italiano di Scienze Farmacologiche in 1955.Application In Synthesis of N,N-Diethylsalicylamide This article mentions the following:

Only doses above the therapeutic ones caused some transient hypotensive effect (more intense by doses of more than 50 mg./kg.): there was also a connection between the chem. constitution of the drug and the hypotensive effect, as for toxicity. N-diethylsalicylamide caused hypertension after a transient hypotension. As to respiration, diacetylgentisic acid and o-diethylaminoethoxybenzamide caused an increase of the amplitude, and salicoyl hydrazide and salicylamide, at higher doses, its decrease; N-diethylsalicylamide (from 30 mg./kg.) increased the respiratory frequency. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Application In Synthesis of N,N-Diethylsalicylamide).

N,N-Diethylsalicylamide (cas: 19311-91-2) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Application In Synthesis of N,N-Diethylsalicylamide

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Synthesis and in vitro biological evaluation of pyrazole group-containing analogues for PDE10A was written by Li, Junfeng;Jin, Hongjun;Zhou, Haiying;Rothfuss, Justin;Tu, Zhude. And the article was included in MedChemComm in 2013.Computed Properties of C9H10BrNO2 This article mentions the following:

Twenty eight new analogs were synthesized by optimizing the structure of MP-10 and their in vitro binding affinities towards PDE10 Å, PDE3A/B, and PDE4A/B were determined Among these new analogs are very potent towards PDE10 Å and have IC₅₀ values of 0.40 ± 0.02, 0.28 ± 0.06, 1.82 ± 0.25, 0.24 ± 0.05, 0.36 ± 0.03 and 1.78 ± 0.03 nM, resp.; these six compounds displayed high selectivity for PDE10 Å vs. PDE3A/3B/4A/4B. The promising compounds will be further validated in vivo to identify PDE10 Å imaging tracers. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Computed Properties of C9H10BrNO2).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well. Thus amides can participate in hydrogen bonding with water and other protic solvents; the oxygen atom can accept hydrogen bonds from water and the N–H hydrogen atoms can donate H-bonds. The presence of the amide group –C(=O)N– is generally easily established, at least in small molecules. It can be distinguished from nitro and cyano groups in IR spectra. Amides exhibit a moderately intense νCO band near 1650 cm−1. By 1H NMR spectroscopy, CONHR signals occur at low fields. In X-ray crystallography, the C(=O)N center together with the three immediately adjacent atoms characteristically define a plane.Computed Properties of C9H10BrNO2

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Tf₂O/TTBP (2,4,6-Tri-tert-butylpyrimidine): An Alternative Amide Activation System for the Direct Transformations of Both Tertiary and Secondary Amides was written by He, Qian;Ye, Jian-Liang;Xu, Fang-Fang;Geng, Hui;Chen, Ting-Ting;Chen, Hang;Huang, Pei-Qiang. And the article was included in Journal of Organic Chemistry in 2021.Reference of 13255-50-0 This article mentions the following:

Ten types of Tf₂O/TTBP-mediated amide transformation reactions were investigated. The results showed that compared with pyridine derivatives 2,6-di-tert-butyl-4-methylpyridine (DTBMP) and 2-fluoropyridine (2-F-Pyr.), TTBP can serve as an alternative amide activation system for the direct transformation of both secondary and tertiary amides. For most surveyed examples, higher or comparable yields were generally obtained. In addition, Tf₂O/TTBP combination was used to promote the condensation reactions of 2-(tert-butyldimethylsilyloxy)furan (TBSOF) with both tertiary and secondary amides, the one-pot reductive Bischler-Napieralski-type reaction of tertiary lactams, and Movassaghi and Hill’s modern version of the Bischler-Napieralski reaction. The value of the Tf₂O/TTBP-based methodol. was further demonstrated by the concise and high-yielding syntheses of several natural products. In the experiment, the researchers used many compounds, for example, 4-Formyl-N-isopropylbenzamide (cas: 13255-50-0Reference of 13255-50-0).

4-Formyl-N-isopropylbenzamide (cas: 13255-50-0) belongs to amides. The solubilities of amides and esters are roughly comparable. Typically amides are less soluble than comparable amines and carboxylic acids since these compounds can both donate and accept hydrogen bonds. Tertiary amides, with the important exception of N,N-dimethylformamide, exhibit low solubility in water. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Reference of 13255-50-0

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Hydrosilane-Assisted Synthesis of Urea Derivatives from CO₂ and Amines was written by Zhao, Yulei;Guo, Xuqiang;Si, Zhiyao;Hu, Yanan;Sun, Ying;Liu, Yunlin;Ji, Zhongyin;You, Jinmao. And the article was included in Journal of Organic Chemistry in 2020.Quality Control of 1,3-Dicyclohexylurea This article mentions the following:

A methodol. employing CO₂, amines, and phenylsilane was discussed to access aryl- or alkyl-substituted urea derivatives This procedure was characterized by adopting hydrosilane to promote the formation of ureas directly, without the need to prepare silylamines in advance. Control reactions suggested that FeCl₃ was a favorable additive for the generation of ureas, and this 1,5,7-triazabicyclo[4.4.0]dec-5-ene-catalyzed reaction might proceed through nucleophilic addition, silicon migration, and the subsequent formal substitution of silylcarbamate. In the experiment, the researchers used many compounds, for example, 1,3-Dicyclohexylurea (cas: 2387-23-7Quality Control of 1,3-Dicyclohexylurea).

1,3-Dicyclohexylurea (cas: 2387-23-7) belongs to amides. Amides include many other important biological compounds, as well as many drugs like paracetamol, penicillin and LSD. Low-molecular-weight amides, such as dimethylformamide, are common solvents. In simple aromatic amides, fragmentation occurs on both sides of the carbonyl group. If a hydrogen is available in N-substituted aromatic amides, it tends to migrate and form an aromatic amine and the loss of a ketene.Quality Control of 1,3-Dicyclohexylurea

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Direct Access to Aryl Bis(trifluoromethyl)carbinols from Aryl Bromides or Fluorosulfates: Palladium-Catalyzed Carbonylation was written by Domino, Katrine;Veryser, Cedrick;Wahlqvist, Benjamin A.;Gaardbo, Cecilie;Neumann, Karoline T.;Daasbjerg, Kim;De Borggraeve, Wim M.;Skrydstrup, Troels. And the article was included in Angewandte Chemie, International Edition in 2018.Category: amides-buliding-blocks This article mentions the following:

A palladium-catalyzed carbonylative approach for the direct conversion of (hetero)aryl bromides into their α,α-bis(trifluoromethyl)carbinols is described, and it employs only stoichiometric amounts of carbon monoxide and trifluoromethyltrimethylsilane. In addition, aryl fluorosulfates proved highly compatible with these reaction conditions. The method is tolerant of a diverse set of functional groups, and it is adaptable to late-stage carbon-isotope labeling. In the experiment, the researchers used many compounds, for example, 4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2Category: amides-buliding-blocks).

4-Bromo-N-methoxy-N-methylbenzamide (cas: 192436-83-2) belongs to amides. Compared to amines, amides are very weak bases and do not have clearly defined acid–base properties in water. On the other hand, amides are much stronger bases than esters, aldehydes, and ketones. As a result of interactions such as these, the water solubility of amides is greater than that of corresponding hydrocarbons. These hydrogen bonds are also have an important role in the secondary structure of proteins.Category: amides-buliding-blocks

Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics