Category: 21778-81-4

Ghosh, Avipsa; Walker, James A.; Ellern, Arkady; Stanley, Levi M. published the article 《Coupling Catalytic Alkene Hydroacylation and α-Arylation: Enantioselective Synthesis of Heterocyclic Ketones with α-Chiral Quaternary Stereocenters》. Keywords: alkene intramol hydroacylation enantioselective arylation nickel NHC catalyst; heterocyclic ketone chiral quaternary stereocenter stereoselective preparation.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Safety of 5-Methoxy-1H-indole-2-carbaldehyde. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:21778-81-4) here.

We report a strategy that combines alkene hydroacylation and enantioselective α-(hetero)arylation reactions to form a wide variety of nitrogen-containing heterocyclic ketones bearing α-chiral quaternary stereogenic centers. Exo-selective, intramol. Ni-catalyzed hydroacylations of N-homoallylindole- and N-homoallylpyrrole-2-carboxaldehydes form α-substituted six-membered heterocyclic ketones in up to 95% yield, while N-heterocyclic carbene (NHC) catalyzed hydroacylations of N-allylindole- and N-allylpyrrole-2-carboxaldehydes form α-substituted five-membered heterocyclic ketones in up to 99% yield. The racemic five- and six-membered products of Ni- and NHC-catalyzed hydroacylation reactions are readily transformed into heterocyclic ketones containing an α-chiral quaternary stereogenic center by enantioselective Ni-catalyzed α-arylation and α-heteroarylation reactions. The chiral, nonracemic products formed through a combination of alkene hydroacylation and α-(hetero)arylation reactions are formed in moderate to high yields (44-99%) with excellent enantioselectivities (typically >95% ee). The identity of the precatalyst for Ni-catalyzed α-(hetero)arylation is dictated by the identity of the α-substituted heterocyclic ketone starting material. α-(Hetero)arylations of six-membered heterocyclic ketones occur at 65-85 °C in the presence of a catalyst generated in situ from Ni(COD)2 and (R)-BINAP or (R)-DIFLUORPHOS. α-(Hetero)arylation of five-membered heterocyclic ketones must be conducted at room temperature in the presence of an [((R)-BINAP)Ni(η2-NC-Ph)] precatalyst or a catalyst generated in situ from Ni(COD)2, (R)-DIFLUORPHOS, and benzonitrile.

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Computed Properties of C10H9NO2. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about 5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles: Relationships between Structure and Cytotoxicity for Analogues Bearing Different DNA Minor Groove Binding Subunits. Author is Atwell, Graham J.; Milbank, Jared J. B.; Wilson, William R.; Hogg, Alison; Denny, William A..

A series of 5-amino-seco-CBI compounds, designed for use as effectors for prodrugs, were prepared to study structure-activity relationships for the cytotoxicity of side chain analogs. Compounds were prepared by coupling 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benz[e]indole to appropriate carboxylic acids, followed by nitro group reduction, or by coupling suitable 5-amino-protected indolines to α,β-unsaturated acids, followed by deblocking. These AT-specific DNA alkylating agents were evaluated for cytotoxicity in a series of tumor cell lines (AA8, UV4, EMT6, SKOV3). For those analogs bearing an indolecarbonyl side chain, the 5′-methoxy derivative was the most cytotoxic (IC50 1.3 nM in AA8 cells, 4 h exposure), comparable to that of the parent CBI-TMI (5′,6′,7′-trimethoxyindole) derivative (IC50 0.46 nM in the above assay). A subset of solubilized derivatives bearing O(CH2)2NMe2 substituents were about 10-fold less potent. For compounds containing an acryloyl linker in the side chain, the 4′-methoxycinnamoyl derivative proved the most cytotoxic (IC50 0.09 nM in the above assay). A number of these 5-amino-seco-CBI-TMI analogs (including the solubilized compounds) are of interest both as cytotoxins and as components of amine-based prodrugs designed for tumor-specific activation.

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Palmer, Brian D.; Thompson, Andrew M.; Booth, R. John; Dobrusin, Ellen M.; Kraker, Alan J.; Lee, Ho H.; Lunney, Elizabeth A.; Mitchell, Lorna H.; Ortwine, Daniel F.; Smaill, Jeff B.; Swan, Leesa M.; Denny, William A. published an article about the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4,SMILESS:O=CC(N1)=CC2=C1C=CC(OC)=C2 ).Application of 21778-81-4. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:21778-81-4) through the article.

High-throughput screening has identified a novel class of inhibitors of the checkpoint kinase Wee1, which have potential for use in cancer chemotherapy. These inhibitors, e.g. I (R = H, 2-FC6H4, 3-NCC6H4, 2,6-Br2C6H3, 2-thienyl, 3-pyrrolyl, 3-pyridyl, etc.), are based on a 4-phenylpyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione template and have been shown by X-ray crystallog. to bind at the ATP site of the enzyme. An extensive study of the effects of substitution around this template has been carried out, which has identified substituents which lead to improvements in potency and selectivity for Wee1. While retention of the maleimide ring and pendant 4-Ph group is necessary for potency, replacement of the carbazole nitrogen by oxygen is well tolerated and results in improved Wee1 selectivity against the related checkpoint kinase Chk1. Wee1 potency and selectivity are also enhanced by the incorporation of lipophilic functionality at the 2′-position of the 4-Ph ring, and Wee1 selectivity against Chk1 is favored by C3-C5 alkyl substitution of the carbazole nitrogen. These studies provide a basis for the design of active analogs of the pyrrolocarbazole lead with improved phys. properties.

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SDS of cas: 21778-81-4. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Efficient selective synthesis of 2-substituted indoles from complex-base-promoted arynic cyclizations. Author is Kuehn-Caubere, Catherine; Rodriguez, Ivan; Pfeiffer, Bruno; Renard, Pierre; Caubere, Paul.

Indoles I [R = 5-MeO, 5-Me, 5-F, 7-Me, 5-MeO, 5-Cl, H; R1 = H, MeO; R2 = n-Pr, i-Pr, allyl, (CH2)2NEt2, (CH2)2NMe2, (CH2)2OEt, MeO] were efficiently obtained by selective arynic cyclization of halogenated aryl imines, e.g. 3,4-Cl(MeO)C6H3N:CMeCH2CH2CH2Me, in the presence of the complex-base NaNH2-Me3CONa. (Mercaptopropyl)indoles II (R = 5-OH, 7-OH; R3 = H, Me, CH2Ph, CH2CO2Et) were prepared by PhCH2SH-AlCl3 promoted opening of tetrahydrothiopyranoindoles which were also obtained from arynic cyclization of imines.

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Wang, Lin-Xuan; Qiu, Bin; An, Xiao-De; Dong, Pei-Zhen; Liu, Rui-Bin; Xiao, Jian published an article about the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4,SMILESS:O=CC(N1)=CC2=C1C=CC(OC)=C2 ).Formula: C10H9NO2. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:21778-81-4) through the article.

An unprecedented organocatalytic cascade aldimine condensation/[1,6]-hydride transfer/Mannich-type cyclization of indole-2-carbaldehydes with o-aminoanilines was developed to assemble polycyclic indole-2,3-fused diazocanes in one step. This novel methodol. featured high step- and atom-economy, was redox-neutral and metal-free, and occurred at room temperature It opened a new window for the application of hydride transfer chem. in constructing medium-sized ring structures.

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Reference of 5-Methoxy-1H-indole-2-carbaldehyde. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Catalysis based on C-I···π halogen bonds: electrophilic activation of 2-alkenylindoles by cationic halogen-bond donors for [4+2] cycloadditions. Author is Kuwano, Satoru; Suzuki, Takumi; Yamanaka, Masahiro; Tsutsumi, Ryosuke; Arai, Takayoshi.

Homo- and cross-[4+2] cycloadditions of 2-alkenylindoles catalyzed by cationic halogen-bond donors were developed. Under mild reaction conditions, 3-indolyl-substituted tetrahydrocarbazole derivatives were obtained in good to excellent yields. Exptl. and quantum calculation studies revealed that the electrophilic activation of 2-alkenylindoles was achieved by C-I···π halogen bonds.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about Synthesis of 9H-Pyrrolo[1,2-a]indole and 3H-Pyrrolizine Derivatives via a Phosphine-Catalyzed Umpolung Addition/Intramolecular Wittig Reaction, the main research direction is pyrrolo indole preparation; pyrrolizine preparation; phosphine catalyzed umpolung addition Wittig indole carbaldehyde acetylene dicarboylate.Safety of 5-Methoxy-1H-indole-2-carbaldehyde.

The first umpolung addition/intramol. Wittig reaction, catalytic in phosphine, is described. The in situ phosphine oxide reduction was accomplished by the use of silane and a catalytic amount of bis(4-nitrophenyl)phosphate. This catalytic protocol is applicable to the synthesis of a wide range of functionalized 9H-pyrrolo[1,2-a]indoles and pyrrolizines (18 examples, 70-98% yields).

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Synthetic Route of C10H9NO2. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: 5-Methoxy-1H-indole-2-carbaldehyde, is researched, Molecular C10H9NO2, CAS is 21778-81-4, about One-pot asymmetric synthesis of quaternary pyrroloindolones through a multicatalytic N-allylation/hydroacylation sequence. Author is Lu, Hong; Lin, Jun-Bing; Liu, Jin-Yu; Xu, Peng-Fei.

An intramol., quaternary-C-center-forming hydroacylation of α-substituted acrylates was discovered. This interesting transformation can be readily incorporated into a multicatalytic tandem process enabled by a combination of nucleophilic tertiary amine and N-heterocyclic carbene catalysis. With no addnl. stoichiometric base required, this transformation affords quaternary pyrroloindolones with high levels of enantioselectivity.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 21778-81-4, is researched, SMILESS is O=CC(N1)=CC2=C1C=CC(OC)=C2, Molecular C10H9NO2Journal, RSC Advances called I2/DMSO-catalyzed one-pot approach for the synthesis of 1,3,4-selenadiazoles, Author is Bowroju, Suresh Kuarm; Bavanthula, Rajitha, the main research direction is arylaldehyde hydrazide selenium iodine catalyst one pot cascade reaction; diaryl selenadiazole preparation; hetroarylaldehyde hydrazide selenium iodine catalyst one pot cascade reaction; diheteroaryl selenadiazole preparation.Related Products of 21778-81-4.

A three-component cascade reaction for the synthesis of 1,3,4-selenadiazoles and their derivatives from arylaldehydes, hydrazine, and elemental selenium by using mol. iodine wais reported. This strategy was operationally simple, well-suited to a wide range of functional groups, and provided the desired products in moderate to excellent yields. The proposed mechanism predicted that the reaction tolerated a radical process.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 21778-81-4, is researched, Molecular C10H9NO2, about Asymmetric construction of polycyclic indole derivatives with different ring connectivities by an organocatalysis triggered two-step sequence, the main research direction is polycyclic indole preparation regioselective stereoselective; hemiacetal indole nitroolefin tandem Michael addition alkylation organocatalysis.Application of 21778-81-4.

An organocatalysis triggered highly regio- and stereoselective two-step sequence between hemiacetals and indole-containing nitroolefins was developed. The key to the success of this sequence was the intramol. oxocarbenium ion induced collective alkylation at the C3, C2, or N1-position of the indole moiety, resp., providing biol. important polycyclic indole derivatives with different ring connectivities. An unexpected epimerization was observed during the C3-alkylation process, which generated products with different relative configurations compared with the C2- and N1-alkylation products.

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