Tag: M.W=200-250

Leth, Lars A.; Glaus, Florian; Meazza, Marta; Fu, Liang; Thogersen, Mathias K.; Bitsch, Emma A.; Jorgensen, Karl Anker published the artcile< Decarboxylative [4+2] Cycloaddition by Synergistic Palladium and Organocatalysis>, Product Details of C9H7BrO, the main research area is vinyl tetrahydroquinoline preparation decarboxylative cycloaddition palladium organocatalyst; asymmetric catalysis; cycloaddition; decarboxylation; heterocycles; synergistic catalysis.

A novel reaction based on synergistic catalysis, combining palladium- and organocatalysis was developed. The palladium catalyst activates vinyl benzoxazinanones via a decarboxylation to undergo a [4+2] cycloaddition with iminium-ion activated α,β-unsaturated aldehydes. The reaction proceeds for a number of combinations of vinyl benzoxazinanones reacting with α,β-unsaturated aldehydes, providing highly substituted vinyl tetrahydroquinolines in good to high yields, and excellent enantio- and diastereoselectivities (>98% ee and >20:1 d.r.). The palladium catalyst used in the synergistic catalysis can be re-used in a one-pot sequential coupling reaction with an aromatic boronic acid forming the coupling product in 95% yield, >20:1 d.r. and 99% ee.

Angewandte Chemie, International Edition published new progress about [4+2] Cycloaddition reaction. 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Product Details of C9H7BrO.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Tran, Cong Chi; Kawaguchi, Shin-ichi; Sato, Fumiya; Nomoto, Akihiro; Ogawa, Akiya published the artcile< Photoinduced Cyclizations of o-Diisocyanoarenes with Organic Diselenides and Thiols that Afford Chalcogenated Quinoxalines>, Electric Literature of 401-78-5, the main research area is diselenide diisocyanoarene photoinduced cyclization light; bisselanyl quinoxaline preparation; thiol diisocyanoarene photoinduced cyclization light; thiolated quinoxaline preparation.

This study describes the syntheses of 2,3-bis(selanyl)quinoxalines via the photoinduced cyclizations of o-diisocyanoarenes with diaryl or dialkyl diselenides, in addition to providing a detailed discussion of the corresponding mechanism and revealing that the developed procedure can also be applied to prepare 2-thiolated quinoxaline derivatives from o-diisocyanoarenes and thiols. The developed technique does not need the use of additives or metal catalysts and features the advantages of a high conversion, a broad substrate scope, and mild reaction conditions, thereby rendering it a valuable addition to the quinoxaline synthesis toolbox.

Journal of Organic Chemistry published new progress about Aromatic nitriles Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Electric Literature of 401-78-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Gao, Limei; Shi, Ruijie; Tian, Yuting; Luo, Xi; Zheng, Yongsheng; Wang, Qiang published the artcile< Synthesis of Pyrazoles through [3+2] Cyclization of Nitrile Imines with Cinnamaldehydes Followed by Air Oxidation>, SDS of cas: 3893-18-3, the main research area is pyrazole preparation green chem regioselective; nitrile imine cinnamyl aldehyde cycloaddition oxidation.

An unprecedented [3+2] cycloaddition reaction of in situ generated nitrile imines with cinnamyl aldehydes followed by air oxidation has been successfully developed under mild conditions, providing an efficient approach to multisubstituted pyrazoles (up to 88% yield). Preliminary mechanistic investigation implies that the final product is generated through oxidation in the presence of air. The prominent features of this reaction include mild conditions, simple operation and gram-scale synthesis.

ChemistrySelect published new progress about [3+2] Cycloaddition reaction (regioselective). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, SDS of cas: 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Cong, Zi-Song; Li, Yang-Guo; Du, Guang-Fen; Gu, Cheng-Zhi; Dai, Bin; He, Lin published the artcile< N-Heterocyclic carbene-catalyzed sulfa-Michael addition of enals>, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde, the main research area is enal thiol sulfa Michael addition nitrogen heterocyclic carbene catalyst.

An efficient N-heterocyclic carbene (NHC) catalyzed sulfa-Michael addition (SMA) between enals and thiols has been developed. Under the catalysis of 10 mol% stable free carbene IPr and with 20 mol% hexafluoroisopropanol (HFIP) as an additive, enals react with a variety of thiols to afford the SMA adducts in 54-98% yields. In this process, the free carbene preferentially interacts with thiols through hydrogen-bonding and no NHC-catalyzed extended Umpolung transformations were observed

Chemical Communications (Cambridge, United Kingdom) published new progress about Michael reaction (sulfa). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Recommanded Product: 3-(4-Bromophenyl)acrylaldehyde.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Estrada, Carl D.; Ang, Hwee Ting; Vetter, Kim-Marie; Ponich, Ashley A.; Hall, Dennis G. published the artcile< Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning>, COA of Formula: C10H11BrO2, the main research area is diol benzyl halide boron acid catalyst enantioselective alkylation desymmetrization; alc preparation.

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chair-like six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed “”methyl blocker”” on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodol. affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Journal of the American Chemical Society published new progress about Alcohols, chiral Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 14062-30-7 belongs to class bromides-buliding-blocks, and the molecular formula is C10H11BrO2, COA of Formula: C10H11BrO2.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Feng, Xin; Cui, Hai-Lei; Xu, Shi; Wu, Li; Chen, Ying-Chun published the artcile< Organocatalytic Direct Vinylogous Michael Addition of α,β-Unsaturated γ-Butyrolactam to α,β-Unsaturated Aldehydes and an Illustration to Scaffold Diversity Synthesis [Erratum to document cited in CA153:600892]>, Reference of 3893-18-3, the main research area is erratum alkyl butyrolactam stereoselective preparation; unsaturated butyrolactam aldehyde Michael addition erratum; enantioselective diastereoselective regioselective chemoselective Michael addition erratum; alkaloid stereoselective preparation erratum; butyrolactam reductive amination intramol aza Michael addition erratum; diastereoselective reductive radical conjugate addition cyclization erratum.

On pages S11, S65, and S68 of the Supporting Information, data for compound 9k and its diastereomer 9k’ were mismatched; the corrected Supporting information is given.

Chemistry – A European Journal published new progress about Alkaloids Role: PRP (Properties), RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 3893-18-3 belongs to class bromides-buliding-blocks, and the molecular formula is C9H7BrO, Reference of 3893-18-3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Liu, Wenwu; Wu, Limeng; Li, Deping; Huang, Yaoguang; Liu, Mingyue; Liu, Wenjie; Tian, Caizhi; Liu, Xin; Jiang, Xiaowen; Hu, Xiaolong; Gao, Xudong; Xu, Zihua; Lu, Hongyuan; Zhao, Qingchun published the artcile< Discovery of novel tacrine derivatives as potent antiproliferative agents with CDKs inhibitory property>, Application In Synthesis of 20776-50-5, the main research area is human colon lung cancer CDK9 antiproliferative anticancer tacrine derivative; AChE; CDK2; CDK9; Cancer therapeutics; Tacrine.

Tacrine was the first approved drug by the FDA for the treatment of Alzheimer′s disease (AD) but was withdrawn from the market due to its dose-dependent hepatotoxicity. Herein, we describe our efforts toward the discovery of a novel series of tacrine derivatives for cancer therapeutics. Intensive structural modifications of tacrine led to the identification of N-(4-{9-[(3S)-3-aminopyrrolidin-1-yl]-5,6,7,8-tetrahydroacridin-2-yl}pyridin-2-yl)cyclopropanecarboxamide hydrochloride ((S)-45, ZLWT-37) as a potent antiproliferative agent (GI50 = 0.029 μM for HCT116). In addition, ZLWT-37 exhibited lower inhibitory activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) compared to tacrine. The in vitro studies demonstrated that ZLWT-37 could significantly induce apoptosis and arrest the cell cycle in the G2/M phase in HCT116 cells. The in vivo studies revealed that compound ZLWT-37 showed excellent antitumor efficacy in HCT116 xenograft tumor model and favorable pharmacokinetics profiles (F% = 28.70%) as well as low toxicity in the acute toxicity test with a median LD (LD50) of 380.3 mg/kg. Encouragingly, ZLWT-37 had no obvious hepatotoxicity, nephrotoxicity, and hematol. toxicity. Kinase assay suggested that ZLWT-37 possessed potent cyclin-dependent kinase 9 (CDK9) inhibitory activity (IC50 = 0.002 μM) and good selectivity over CDK2 (IC50 = 0.054 μM). Collectively, these findings indicate that compound ZLWT-37 is a promising anti-cancer agent that deserves further preclin. evaluation.

Bioorganic Chemistry published new progress about Antiproliferative agents. 20776-50-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H6BrNO2, Application In Synthesis of 20776-50-5.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Capel, Estefania; Luis-Barrera, Javier; Sorazu, Ana; Uria, Uxue; Prieto, Liher; Reyes, Efraim; Carrillo, Luisa; Vicario, Jose L. published the artcile< Transannular Approach to 2,3-Dihydropyrrolo[1,2-b]isoquinolin-5(1H)-ones through Bronsted Acid-Catalyzed Amidohalogenation>, HPLC of Formula: 6942-39-8, the main research area is pyrroloisoquinolinone preparation; benzo fused ene lactam amidohalogenation elimination Bronsted acid catalyst.

A transannular approach has been developed for the construction of pyrrolo[1,2-b]isoquinolinones I (R1 = H, F, Cl, Me, OMe, etc.; R2 = H, F, etc.; R3 = H, Me, etc.; R4 = H, F) starting from benzo-fused nine-membered enelactams II. This process takes place in the presence of a halogenating agent and under Bronsted acid catalysis and proceeds via a transannular amidohalogenation, followed by elimination. The reaction has been found to be wide in scope, enabling the formation of a variety of tricyclic products I in good overall yield, regardless of the substitution pattern in the initial lactam substrate. The reaction has also been applied to the total synthesis of a reported topoisomerase I inhibitor and to the formal synthesis of rosettacin. Further extension of this methodol. allows the preparation of 10-iodopyrrolo[1,2-b]isoquinolinones III (R1 = H, Me; R2 = H, F; R3 = H, F, Me, OMe) by using an excess of halogenating agent and these compounds can be further manipulated through standard Suzuki coupling chem. into a variety of 10-aryl-substituted pyrrolo[1,2-b]isoquinolinones IV.

Journal of Organic Chemistry published new progress about Alkenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 6942-39-8 belongs to class bromides-buliding-blocks, and the molecular formula is C8H6BrFO2, HPLC of Formula: 6942-39-8.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Zhang, Lei; Hu, Xile published the artcile< Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds>, Formula: C7H4BrF3, the main research area is toluene aryl bromide nickel catayst electrochem arylation; arylmethylbenzene preparation.

Convergent paired electrosynthesis is an energy-efficient approach in organic synthesis; however, it is limited by the difficulty to match the innate redox properties of reaction partners. Here we use nickel catalysis to cross-couple the two intermediates generated at the two opposite electrodes of an electrochem. cell, achieving direct arylation of benzylic C-H bonds. This method yields a diverse set of diarylmethanes, which are important structural motifs in medicinal and materials chem. Preliminary mechanistic study suggests oxidation of a benzylic C-H bond, Ni-catalyzed C-C coupling, and reduction of a Ni intermediate as key elements of the catalytic cycle.

Chemical Science published new progress about Alkylarenes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 401-78-5 belongs to class bromides-buliding-blocks, and the molecular formula is C7H4BrF3, Formula: C7H4BrF3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary

Menzel, Karsten; Dimichele, Lisa; Mills, Paul; Frantz, Doug E.; Nelson, Todd D.; Kress, Michael H. published the artcile< Regioselective halogen-metal exchange reaction of 3-substituted 1,2-dibromo arenes: the synthesis of 2-substituted 5-bromobenzoic acids>, Formula: C8H3BrO3, the main research area is substituted dibromoarene isopropylmagnesium chloride regioselective halogen metal exchange; bromoarene substituted preparation; bromobenzoic acid substituted preparation; regioselective halogen metal exchange reagent isopropylmagnesium chloride.

Regioselective halogen-metal exchange reactions using isopropylmagnesium chloride were carried out on 3-substituted 1,2-dibromo arenes, e.g., I. When the 3-substituent was either electron-withdrawing and/or possessed lone pair electrons that enabled chelation of isopropylmagnesium chloride, a high regioselectivity for the halogen-metal exchange adjacent to the 3-substituents resulted.

Synlett published new progress about Aromatic carboxylic acids Role: SPN (Synthetic Preparation), PREP (Preparation) (bromo-). 82-73-5 belongs to class bromides-buliding-blocks, and the molecular formula is C8H3BrO3, Formula: C8H3BrO3.

Referemce:
Bromide – Wikipedia,
bromide – Wiktionary