Tag: 100-200

Reaction of phenol with diethylcarbamoyl chloride in the presence of Lewis acids was written by Isakova, A. P.;Naumov, Yu. A.;Nikeryasova, S. V.;Stepanova, A. A.. And the article was included in Zhurnal Organicheskoi Khimii in 1982.Related Products of 19311-91-2 This article mentions the following:

In the presence of SnCl₄ or AlCl₃, Et₂NCOCl reacted with PhOH to give Et₂NCO₂Ph, which at 175-80° underwent a Fries rearrangement to give I, II, and III, which were inactive as pesticides. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Related Products of 19311-91-2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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.Related Products of 19311-91-2

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

Supported palladium catalyzed aminocarbonylation of aryl iodides employing bench-stable CO and NH₃ surrogates was written by Shaifali;Sheetal;Bains, Rohit;Kumar, Ajay;Ram, Shankar;Das, Pralay. And the article was included in Organic & Biomolecular Chemistry in 2020.SDS of cas: 2670-38-4 This article mentions the following:

A simple, efficient and phosphine free protocol for carbonylative synthesis of primary aromatic amides under polystyrene supported palladium (Pd@PS) nanoparticle (NP) catalyzed conditions has been demonstrated. Herein, instead of using two toxic and difficult to handle gases simultaneously, we have employed the solid, economical, bench stable oxalic acid as the CO source and ammonium carbamate as the NH₃ source in a single pot reaction. For the first time, we have applied two non-gaseous surrogates simultaneously under heterogeneous catalyst (Pd@PS) conditions for the synthesis of primary amides using an easy to handle double-vial (DV) system. The developed strategy showed a good functional group tolerance towards a wide range of aryl iodides and afforded primary aromatic amides in good yields. The Pd@PS catalyst was easy to sep. and can be recycled up to four consecutive runs with small loss in catalytic activity. We have successfully extended the scope of the methodol. to the synthesis of isoindole-1,3-diones from 1,2-dihalobenzene, 2-halobenzoates and 2-halobenzoic acid following double and single carbonylative cyclization approaches. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4SDS of cas: 2670-38-4).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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. Amides can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.SDS of cas: 2670-38-4

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

Redox Cyclization of Amides and Sulfonamides with Nitrous Oxide for Direct Synthesis of Heterocycles was written by Lai, Zhencheng;Wang, Chaorong;Li, Jiaming;Cui, Sunliang. And the article was included in Organic Letters in 2020.Electric Literature of C9H13NO2S This article mentions the following:

A redox cyclization of amides R¹C(O)NHR² (R¹ = C₆H₅, 1-naphthyl, 5-methylthiophen-2-yl, etc.; R² = Me, t-Bu, cyclopropyl, etc.) and sulfonamides 4-R³C₆H₄S(O)₂NHR⁴ (R³ = H, Me, t-Bu, Ph, OMe, Cl; R⁴ = Me, t-Bu, cyclopropyl, etc.) with nitrous oxide (N₂O) for the direct synthesis of heterocycles, e.g., I has been described. Various amides and sulfonamides could undergo directed ortho metalation (DoM) by treatment with BuLi, and the lithium intermediate could be trapped by N₂O gas to achieve redox cyclization. N₂O serves as an N-atom donor to mediate the intramol. coupling of lithium species toward heterocycle formation with free external oxidant. This protocol offers a direct synthesis of heterocycles with features of readily available starting materials, simple operation, and a broad substrate scope. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Electric Literature of C9H13NO2S).

N-Isopropylbenzenesulfonamide (cas: 5339-69-5) 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 can be recrystallised from large quantities of water, ethanol, ethanol/ether, aqueous ethanol, chloroform/toluene, chloroform or acetic acid. The likely impurities are the parent acids or the alkyl esters from which they have been made. The former can be removed by thorough washing with aqueous ammonia followed by recrystallisation, whereas elimination of the latter is by trituration or recrystallisation from an organic solvent.Electric Literature of C9H13NO2S

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

Screening of ligands for the Ullmann synthesis of electron-rich diaryl ethers was written by Otto, Nicola;Opatz, Till. And the article was included in Beilstein Journal of Organic Chemistry in 2012.Application In Synthesis of N1,N2-Dimethoxy-N1,N2-dimethyloxalamide This article mentions the following:

In the search for ligands for the Ullmann diaryl ether synthesis, permitting the coupling of electron-rich aryl bromides at relatively low temperatures, 56 structurally diverse multidentate ligands were screened in a model system that uses copper iodide in acetonitrile with potassium phosphate as the base. The ligands differed largely in their performance, but no privileged structural class could be identified. In the experiment, the researchers used many compounds, for example, N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1Application In Synthesis of N1,N2-Dimethoxy-N1,N2-dimethyloxalamide).

N1,N2-Dimethoxy-N1,N2-dimethyloxalamide (cas: 106675-70-1) 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. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Application In Synthesis of N1,N2-Dimethoxy-N1,N2-dimethyloxalamide

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

The Tetraethylphosphorodiamidate (OP(O)(NEt₂)₂) Directed Metalation Group (DMG). Directed ortho and Lateral Metalation and the Phospha Anionic Fries Rearrangement was written by Alessi, Manlio;Patel, Jignesh J.;Zumbansen, Kristina;Snieckus, Victor. And the article was included in Organic Letters in 2020.Application of 19311-91-2 This article mentions the following:

We report on the tetraethylphosphorodiamidate (-OP(O)(NEt₂)₂) group as an effective directed metalation group (DMG). Directed ortho-lithiation-electrophile quench of ArOP(O)(NEt₂)₂ (1a–e; Ar = substituted Ph, 2-naphthyl) provides a general synthesis of ortho-substituted aryl and naphthyl phosphorodiamidates. We also describe the phospha anionic ortho-Fries (AoF) rearrangement of the phosphorodiamidates 1a,b, giving phosphonates 3-R-2-[P(O)(NEt₂)₂]C₆H₃OH its vinylogous counterpart to the ortho-tolyl phosphorodiamidates. Intermol. competition experiments demonstrate the approx. equal DMG strength of the -OP(O)(NEt₂)₂ and the most powerful OCONEt₂ groups. In the experiment, the researchers used many compounds, for example, N,N-Diethylsalicylamide (cas: 19311-91-2Application of 19311-91-2).

N,N-Diethylsalicylamide (cas: 19311-91-2) 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. 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.Application of 19311-91-2

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

Discovery of potent nucleotide pyrophosphatase/phosphodiesterase3 (NPP3) inhibitors with ancillary carbonic anhydrase inhibition for cancer (immuno)therapy was written by Lee, Sang-Yong;Namasivayam, Vigneshwaran;Boshta, Nader M.;Perotti, Arianna;Mirza, Salahuddin;Bua, Silvia;Supuran, Claudiu T.;Mueller, Christa E.. And the article was included in RSC Medicinal Chemistry in 2021.Synthetic Route of C7H10N2O2S This article mentions the following:

Nucleotide pyrophosphatase/phosphodiesterase3 (NPP3) catalyzes the hydrolysis of extracellular nucleotides. It is expressed by immune cells and some carcinomas, e.g. of kidney and colon. Together with ecto-5′-nucleotidase (CD73), NPP3 produces immunosuppressive, cancer-promoting adenosine, and has therefore been proposed as a target for cancer therapy. Here we report on the discovery of 4-[(4-methylphthalazin-1-yl)amino]benzenesulfonamide (1) as an inhibitor of human NPP3 identified by compound library screening. Subsequent structure-activity relationship (SAR) studies led to the potent competitive NPP3 inhibitor 2-methyl-5-{4-[(4-sulfamoylphenyl)amino]phthalazin-1-yl}benzenesulfonamide (23, K_i 53.7 nM vs. the natural substrate ATP). Docking studies predicted its binding pose and interactions. While 23 displayed high selectivity vs. other ecto-nucleotidases, it showed ancillary inhibition of two proposed anti-cancer targets, the carbonic anhydrases CA-II (K_i 74.7 nM) and CA-IX (K_i 20.3 nM). Thus, 23 may act as multi-target anti-cancer drug. SARs for NPP3 were steeper than for CAs leading to the identification of potent dual CA-II/CA-IX (e.g.34) as well as selective CA-IX inhibitors (e.g.31). In the experiment, the researchers used many compounds, for example, 4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4Synthetic Route of C7H10N2O2S).

4-Amino-3-methylbenzenesulfonamide (cas: 53297-70-4) 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. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.Synthetic Route of C7H10N2O2S

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

Novel acylureidoindolin-2-one derivatives as dual Aurora B/FLT3 inhibitors for the treatment of acute myeloid leukemia was written by Jagtap, Ajit Dhananjay;Chang, Pei-Teh;Liu, Jia-Rong;Wang, Hsiao-Chun;Kondekar, Nagendra B.;Shen, Li-Jiuan;Tseng, Hsiang-Wen;Chen, Grace Shiahuy;Chern, Ji-Wang. And the article was included in European Journal of Medicinal Chemistry in 2014.Safety of 3,4-Dichlorobenzamide This article mentions the following:

A series of 6-acylureido derivatives containing a 3-(pyrrol-2-ylmethylidene)indolin-2-one scaffold were synthesized as potential dual Aurora B/FLT3 inhibitors by replacing the 6-arylureido moiety in 6-arylureidoindolin-2-one-based multi-kinase inhibitors. (Z)-N-(2-(pyrrolidin-1-yl)ethyl)-5-((6-(3-(2-fluoro-4-methoxybenzoyl)ureido)-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide I was identified as a dual Aurora B/FLT3 inhibitor (IC₅₀ = 0.4 nM and 0.5 nM, resp.). Compound I also exhibited potent cytotoxicity with single-digit nanomolar IC₅₀ values against the FLT3 mutant-associated human acute myeloid leukemia (AML) cell lines MV4-11 (FLT3-ITD) and MOLM-13 (FLT3-ITD). Compound I also specifically induced extrinsic apoptosis by inhibiting the phosphorylation of the Aurora B and FLT3 pathways in MOLM-13 cells. Compound I had a moderate pharmacokinetic profile. The mesylate salt of I efficiently inhibited tumor growth and reduced the mortality of BALB/c nude mice (s.c. xenograft model) that had been implanted with AML MOLM-13 cells. Compound 54 is more potent than sunitinib not only against FLT3-WT AML cells but also active against sunitinib-resistant FLT3-ITD AML cells. This study demonstrates the significance of dual Aurora B/FLT3 inhibitors for the development of potential agents to treat AML. In the experiment, the researchers used many compounds, for example, 3,4-Dichlorobenzamide (cas: 2670-38-4Safety of 3,4-Dichlorobenzamide).

3,4-Dichlorobenzamide (cas: 2670-38-4) 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.Safety of 3,4-Dichlorobenzamide

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

Synthesis of 2-(2-Hydroxyaryl)-4H-benzo[e][1,3]oxazin-4-ones by Palladium-Catalyzed C(sp²)-H Hydroxylation via Electro-chemical Oxidation was written by Wu, Hongfeng;An, Qi;He, Chaoyin;Fan, Xiaodong;Guo, Weihao;Zuo, Minghui;Xu, Chunzhao;Guo, Rui;Chu, Wenyi;Sun, Zhizhong. And the article was included in Advanced Synthesis & Catalysis in 2020.Related Products of 49667-22-3 This article mentions the following:

An electrochem. direct ortho-hydroxylation of 2-aryl-4H-benzo[e][1,3]oxazin-4-ones I (R¹ = Ph, 4-chlorophenyl, 2-naphthyl, furan-3-yl, etc.; R² = H, 7-Me, 6-Cl, etc.) was developed with Pd(OAc)₂ as catalyst, oxazine ring as a directing group and Oxone as the hydroxylation reagent. A series of hydroxylation products II (R³ = 2-hydroxyphenyl, 2-hydroxy-4-chlorophenyl, 2-hydroxyfuran-3-yl, etc.) was obtained under mild conditions, and the yields were from medium to good. This method is characterized by good functional group tolerance and a wide range of substrates. More importantly, anodic oxidation is used to avoid the use of potentially toxic and polluting oxidants. A gram-scale direct electrochem. hydroxylation of 2-phenyl-4H-benzo[e][1,3]oxazin-4-one was performed, and the hydroxylation product, 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was applied to synthesize the drug deferasirox. In addition, the single crystal of 2-(2-hydroxyphenyl)-4H-benzo[e][1,3]oxazin-4-one was obtained and determined by X-ray diffraction. Finally, the reaction mechanism was proposed and verified by cyclic voltammetry (CV). This protocol also provides an alternative electrochem. hydroxylation methodol. for the functionalization of mols. In the experiment, the researchers used many compounds, for example, 2-Hydroxy-4-methylbenzamide (cas: 49667-22-3Related Products of 49667-22-3).

2-Hydroxy-4-methylbenzamide (cas: 49667-22-3) 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. 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.Related Products of 49667-22-3

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

Copper-Catalyzed Reactions of Alkenyl Boronic Esters via Chan-Evans-Lam Coupling/Annulation Cascades: Substrate Selective Synthesis of Dihydroquinazolin-4-ones and Polysubstituted Quinolines was written by Li, Yuge;Cao, Zifeng;Wang, Zhijun;Xu, Liang;Wei, Yu. And the article was included in Organic Letters in 2022.COA of Formula: C7H7FN2O This article mentions the following:

Copper-catalyzed cascade cyclization reactions between alkenyl boronic esters BpinC(R)=CH(R¹) [R = H, Me; R¹ = Me; RR¹ = -(CH₂)₅-, -(CH₂)₂O(CH₂)₂-, -(CH₂)₂N(C(O)Ot-Bu)(CH₂)₂-] and N-H-based nucleophiles R²C(O)NHR³ (R² = 2-amino-5-fluorophenyl, 2-amino-3-bromophenyl, 2-aminophenyl, etc.; R³ = H, Me, Ph, Bn, etc.) have been established, providing new approaches for one-pot assembly of azacycles. Following the Chan-Evans-Lam C-N couplings, the cyclization processes occur via divergent pathways based on the utilized substrates, affording hydroamination product dihydroquinazolin-4-ones I (R⁴ = H, 6-Me, 8-Br, 7-F, etc.) or aromatization product quinolines II (R⁵ = Ph, 4-chlorophenyl, Me, etc.; X = H, Cl, Br, F). Via this one-pot C-N coupling/annulation cascade, the target substituted azacycles can be obtained in moderate to good yields in each case. In the experiment, the researchers used many compounds, for example, 2-Amino-4-fluorobenzamide (cas: 119023-25-5COA of Formula: C7H7FN2O).

2-Amino-4-fluorobenzamide (cas: 119023-25-5) 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. Ionic, or saltlike, amides are strongly alkaline compounds ordinarily made by treating ammonia, an amine, or a covalent amide with a reactive metal such as sodium.COA of Formula: C7H7FN2O

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

Transamidation of primary amides with amines catalyzed by zirconocene dichloride was written by Atkinson, Benjamin N.;Chhatwal, A. Rosie;Lomax, Helen V.;Walton, James W.;Williams, Jonathan M. J.. And the article was included in Chemical Communications (Cambridge, United Kingdom) in 2012.Application of 61189-99-9 This article mentions the following:

Zirconocene dichloride has been shown to be an effective catalyst for the transamidation of primary amides with amines in cyclohexane at 80° in 5-24 h. For favorable substrates, the reaction can be performed at temperatures as low as 30°. In the experiment, the researchers used many compounds, for example, 2,2-Diethoxyacetamide (cas: 61189-99-9Application of 61189-99-9).

2,2-Diethoxyacetamide (cas: 61189-99-9) 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. 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.Application of 61189-99-9

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