Category: 118-90-1

Hu, Wenbo published the artcileRhodium(III)-Catalyzed Three-Component Cascade Annulation for Modular Assembly of N-Alkoxylated Isoindolin-1-Ones with Quaternary Carbon Center, Recommanded Product: 2-Methylbenzoic acid, the publication is Advanced Synthesis & Catalysis (2022), 364(15), 2589-2595, database is CAplus.

A cascade C-H activation, annulation and etherification of N-hydroxybenzamides with propargylamines provided a flexible route to N-alkoxylated 3-arylisoindolin-1-ones. Three new bonds (C-C, C-N, and C-O) were generated to afford a series of isoindolin-1-ones bearing a tetrasubstituted carbon in 49-82% yield. The utility of this method was showcased by gram-scale synthesis and synthetic transformations of the product to access structurally diverse isoindolinones.

Advanced Synthesis & Catalysis published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Recommanded Product: 2-Methylbenzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

He, Qiyuan published the artcilePalladium-Catalyzed Site-Selective [5 + 1] Annulation of Aromatic Amides with Alkenes: Acceleration of ¦Â-Hydride Elimination by Maleic Anhydride from Palladacycle, Name: 2-Methylbenzoic acid, the publication is ACS Catalysis (2022), 12(2), 1595-1600, database is CAplus.

The palladium-catalyzed reaction of 2-methylbenzamides with acrylic esters, leading to the production of isoquinolinones, is reported. The reaction occurs exclusively at the ortho Me C-H bond via a six-membered palladacycle and not at the ortho C-H bond via a five-membered palladacycle. A key to the success of the reaction is the use of maleic anhydride as a ligand. Computational analyses suggest that the coordination of the maleic anhydride ligand highly stabilizes the transition state for ¦Â-hydride elimination and accelerates the ¦Â-hydride elimination.

ACS Catalysis published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Name: 2-Methylbenzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Wang, Yangyang published the artcileLigand-Enabled C-H Olefination and Lactonization of Benzoic Acids and Phenylacetic Acids via Palladium Catalyst, Quality Control of 118-90-1, the publication is Organic Letters (2022), 24(3), 821-825, database is CAplus and MEDLINE.

A novel ligand propan-2-one O-(p-tolylcarbamoyl) oxime had been developed to promote C(sp²)-H olefination of benzoic acids and phenylacetic acids via a palladium catalyst. With the subsequent lactonization of the olefinated products through 1,4-addition, a highly monoselective cyclic lactone products of benzopyrones I [R¹ = 5-Me, 7-Cl, 5-F, etc.; R² = CO₂Me, CO₂Et, CO₂Bu, CO₂Bn, C(O)NHCH(CH₃)₂, P(O)(OEt)₂] and benzofuranones II [R³ = 5-Me, 6-MeO, 6-CF₃, etc.; R² = CO₂Me, CO₂Et, CO₂Bu, etc.] were obtained in moderate to excellent yields. The DFT calculation demonstrated that the novel ligand propan-2-one O-(p-tolylcarbamoyl) oxime could lubricate the C-H activation reaction to give cyclic lactone products elegantly.

Organic Letters published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C25H47NO8, Quality Control of 118-90-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Cai, Mingzhong published the artcileRecyclable palladium-catalyzed Suzuki coupling of aromatic triazine esters: A practical one-pot synthesis of aryl ketones from aromatic acids, Application of 2-Methylbenzoic acid, the publication is Synthetic Communications (2022), 52(7), 1079-1090, database is CAplus.

An efficient heterogeneous palladium-catalyzed Suzuki coupling of aromatic triazine esters I (Ar = 4-methylphenyl, naphthalen-1-yl, thiophen-2-yl, etc.) with arylboronic acids Ar¹B(OH)₂ (Ar¹ = Ph, 3,5-dichlorophenyl, furan-2-yl, etc.) has been developed. The reaction proceeds smoothly in toluene at 110¡ãC using 2 mol% of MCM-41-bound bidentate phosphine palladium complex [MCM-41-2P-Pd(OAc)₂] as catalyst and provides a novel and practical method for the synthesis of aryl ketones ArC(O)Ar¹ starting from readily available aromatic acids ArCOOH in a one-pot procedure with moderate to excellent yields. The MCM-41-2P-Pd(OAc)₂ catalyst can be reused at least seven times without any apparent decrease in its catalytic activity.

Synthetic Communications published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Application of 2-Methylbenzoic acid.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Liu, Junkai published the artcileIdentification of new potent anticancer derivatives through simplifying the core structure and modification on their 14- hydroxyl group from oridonin, Quality Control of 118-90-1, the publication is European Journal of Medicinal Chemistry (2022), 114155, database is CAplus and MEDLINE.

The natural product oridonin has the potential to be a broad-spectrum antineoplastic agent. To develop oridonin analogs with high potency, a series of novel oridonin analogs were designed and synthesized by removing the multiple hydroxyl groups of parent compound The representative analogs 14, 19, and 26 (I – III, resp.) exhibited potent anticancer effects against K562, MDA-MB-231, SMMC-7721, and MCF-7 cells. Further structural modification on their 14-OH generated more potent derivatives 16n, 21d, and 28d, resp. (IV – VI, resp.), in which the IC₅₀ value of compound 16n was 50-fold more potent than parent oridonin in K562 cells. Furthermore, compound 16n significantly induced the cell cycle arrest of K562 cells at the G2 phase and increased the fraction of apoptotic cells. Importantly, compounds 16n, 21d, and 28d exhibited good antitumor activities in H22 allograft mice in vivo. These results suggest that compounds 16n, 21d, and 28d deserve further development as promising candidates for the treatment of cancers.

European Journal of Medicinal Chemistry published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Quality Control of 118-90-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zhang, Zeshuai published the artcileSelective N-Monovinylation of Primary Aromatic Amides Using Calcium Carbide as an Alkyne Source, Quality Control of 118-90-1, the publication is ChemistrySelect (2022), 7(26), e202201463, database is CAplus.

An efficient method for the selective N-monovinylation of primary aromatic amides using calcium carbide as an alkyne source was described. A series of N-vinylbenzamides (enamides) RC(O)NHCH=CH₂ [R = Ph, 2-MeC₆H₄, 4-ClMeC₆H₄, etc.] were readily synthesized by this strategy. The salient features for this protocol were the use of inexpensive, easy-to-handle solid alkyne source, high chemoselectivity, transition metal catalyst-free, good functional group tolerance, and simple work-up procedures. These reactions was also be extended to the gram-scale level.

ChemistrySelect published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C18H23OP, Quality Control of 118-90-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Wu, Zhe published the artcileGram-scale synthesis of carboxylic acids via catalytic acceptorless dehydrogenative coupling of alcohols and hydroxides at an ultralow Ru loading, Synthetic Route of 118-90-1, the publication is Applied Catalysis, A: General (2022), 118443, database is CAplus.

Acceptorless dehydrogenative coupling (ADC) of alcs. and water/hydroxides is an emergent and graceful approach to produce carboxylic acids. Therefore, it is of high demand to develop active and practical catalysts/catalytic systems for this attractive transformation. Herein, the design and fabrication of a series of cyclometallated N-heterocyclic carbene-Ru (NHC-Ru) complexes via ligand tuning of [Ru-1], the superior complex in the previous work. Gratifyingly, gram-scale synthesis of carboxylic acids was efficiently enabled at an ultralow Ru loading (62.5 ppm) in open air. Moreover, effects of distinct ancillary NHC ligands and other parameters on this catalytic process were thoroughly studied, while further systematic studies were carried out to provide rationales for the activity trend of [Ru-1]-[Ru-7]. Finally, determination of quant. green metrics illustrated that the present work exhibited superiority over representative literature reports. Hopefully, this study could provide valuable input for researchers who are engaging in metal-catalyzed ADC reactions.

Applied Catalysis, A: General published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C2H2N4O2, Synthetic Route of 118-90-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Gu, Chengyihan published the artcileVisible-light-mediated amidation from carboxylic acids and tertiary amines via C-N cleavage, Quality Control of 118-90-1, the publication is Chemical Communications (Cambridge, United Kingdom) (2022), 58(39), 5873-5876, database is CAplus and MEDLINE.

Synthesis of tertiary amides RC(O)NR₁R₂ [R = Ph, 4-MeC₆H₄, 4-PhC₆H₄, etc.; R¹ = R² = Et, n-Pr; R¹R² = CH₂(CH₂)₃CH₂] via iridium photocatalyzed amidation of carboxylic acids and tertiary amines through C-N bond cleavage was reported. A wide scope of structurally diverse carboxylic acids participated smoothly in the reaction, providing the desired tertiary amides with moderate-to-good yields (up to 93% yield). This amidation strategy provided an alternative way to address the regioselectivity between nucleophilic functional groups, thus complementing the functional group compatibility of classical amidation protocols. Its synthetic robustness was also proved by the late-stage modification of several complex mols. and gram-scale applications.

Chemical Communications (Cambridge, United Kingdom) published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Quality Control of 118-90-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Zuo, Dongxu published the artcileHighly Chemoselective Transamidation of Unactivated Tertiary Amides by Electrophilic N-C(O) Activation by Amide-to-Acyl Iodide Re-routing, Computed Properties of 118-90-1, the publication is Angewandte Chemie, International Edition (2022), 61(24), e202202794, database is CAplus and MEDLINE.

The challenging transamidation of unactivated tertiary amides has been accomplished via cooperative acid/iodide catalysis. Most crucially, the method provides a novel manifold to re-route the reactivity of unactivated N,N-dialkyl amides through reactive acyl iodide intermediates, thus reverting the classical order of reactivity of carboxylic acid derivatives This method provides a direct route to amide-to-amide bond interconversion with excellent chemoselectivity using equivalent amounts of amines. The combination of acid and iodide has been identified as the essential factor to activate the amide C-N bond through electrophilic catalytic activation, enabling the production of new desired transamidated products with wide substrate scope of both unactivated amides and amines, including late-stage functionalization of complex APIs (>80 examples). Authors anticipate that this powerful activation mode of unactivated amide bonds will find broad-ranging applications in chem. synthesis.

Angewandte Chemie, International Edition published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H15ClN2, Computed Properties of 118-90-1.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia

Li, Xin-yang published the artcileDiscovery of N-(1,3,4-thiadiazol-2-yl)benzamide derivatives containing a 6,7-methoxyquinoline structure as novel EGFR/HER-2 dual-target inhibitors against cancer growth and angiogenesis, Formula: C8H8O2, the publication is Bioorganic Chemistry (2022), 105469, database is CAplus and MEDLINE.

Targeting EGFR and HER-2 is an essential direction for cancer treatment. Here, a series of N-(1,3,4-thiadiazol-2-yl)benzamide derivatives containing a 6,7-methoxyquinoline structure was designed and synthesized to serve as EGFR/HER-2 dual-target inhibitors. The kinase assays verified that target compounds could inhibit the kinase activity of EGFR and HER-2 selectively. The results of CCK-8 and 3D cell viability assays confirmed that target compounds had excellent anti-proliferation ability against breast cancer cells (MCF-7 and SK-BR-3) and lung cancer cells (A549 and H1975), particularly against SK-BR-3 cells, while the inhibitory effect on healthy breast cells (MCF-10A) and lung cells (Beas-2B) was weak. Among them, the hit compound YH-9 binded to EGFR and HER-2 stably in mol. dynamics studies. Further studies found that YH-9 could induce the release of cytochrome c and inhibit proliferation by promoting ROS expression in SK-BR-3 cells. Moreover, YH-9 could diminish the secretion of VEGF and bFGF factors in SK-BR-3 cells, then inhibited tube formation and angiogenesis. Notably, YH-9 could effectively inhibit breast cancer growth and angiogenesis with little toxicity in the SK-BR-3 cell xenograft model. Taken together, in vitro and in vivo results revealed that YH-9 had high drug potential as a dual-target inhibitor of EGFR/HER-2 to inhibit breast cancer growth and angiogenesis.

Bioorganic Chemistry published new progress about 118-90-1. 118-90-1 belongs to catalysis-chemistry, auxiliary class Carboxylic acid,Benzene,Natural product, name is 2-Methylbenzoic acid, and the molecular formula is C8H8O2, Formula: C8H8O2.

Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia