Category: 4771-48-6

Huang, Yong; Song, Liangliang; Gong, Lei; Meggers, Eric published the artcile< Asymmetric Synthesis of Hydrocarbazoles Catalyzed by an Octahedral Chiral-at-Rhodium Lewis Acid>, Application In Synthesis of 4771-48-6, the main research area is hydrocarbazole enantioselective synthesis regioselective synthesis; vinylindole carboxylic ester substituted unsaturated acyl imidazole; Diels Alder reaction chiral Rh complex catalyst; Diels-Alder; asymmetric catalysis; chiral-at-metal; hydrocarbazoles; rhodium.

A bis-cyclometalated chiral-at-metal rhodium complex catalyzes the Diels-Alder reaction between N-Boc-protected 3-vinylindoles (Boc=tert-butyloxycarbonyl) and β-carboxylic ester-substituted α,β-unsaturated 2-acyl imidazoles with good-to-excellent regioselectivity (up to 99:1) and excellent diastereoselectivity (>50:1 d.r.) as well as enantioselectivity (92-99 % ee), e. g., I, under optimized conditions. The rhodium catalyst serves as a chiral Lewis acid to activate the 2-acyl imidazole dienophile by two-point binding and overrules the preferred regioselectivity of the uncatalyzed reaction.

Chemistry – An Asian Journal published new progress about Aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhou, Zijun; Li, Yanjun; Gong, Lei; Meggers, Eric published the artcile< Enantioselective 2-Alkylation of 3-Substituted Indoles with Dual Chiral Lewis Acid/Hydrogen-Bond-Mediated Catalyst>, Application In Synthesis of 4771-48-6, the main research area is enantioselective alkylation indole unsaturated acylimidazole chiral cyclometalated iridium complex; bifunctional chiral Lewis acid hydrogen bond mediated alkylation catalyst; pyrroloindole preparation.

A chiral-at-metal bis-cyclometalated iridium complex combines electrophile activation via metal coordination with nucleophile activation through hydrogen bond formation [e.g., indole I + acylimidazole II → III (89% conversion, 98% ee (S)) in presence of Δ-Ir complex IV.BARF]. This new bifunctional chiral Lewis acid/hydrogen-bond-mediated catalyst permits the challenging enantioselective 2-alkylation of 3-substituted indoles with α,β-unsaturated 2-acylimidazoles in up to 99% yield and with up to 98% enantiomeric excess at a catalyst loading of 2 mol %. As an application, the straightforward synthesis of a chiral pyrrolo[1,2-a]indole is demonstrated.

Organic Letters published new progress about Alkylation catalysts, stereoselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Qinghui; Arnst, Kinsie E.; Wang, Yuxi; Kumar, Gyanendra; Ma, Dejian; White, Stephen W.; Miller, Duane D.; Li, Weimin; Li, Wei published the artcile< Structure-Guided Design, Synthesis, and Biological Evaluation of (2-(1H-Indol-3-yl)-1H-imidazol-4-yl)(3,4,5-trimethoxyphenyl) Methanone (ABI-231) Analogues Targeting the Colchicine Binding Site in Tubulin>, Application of C10H9NO, the main research area is ABI 231 analog design synthesis anticancer.

ABI-231 is a potent, orally bioavailable tubulin inhibitor that interacts with the colchicine binding site and is currently undergoing clin. trials for prostate cancer. Guided by the crystal structure of ABI-231 in complex with tubulin, we performed structure-activity relationship studies around the 3-indole moiety that led to the discovery of several potent ABI-231 analogs, most notably 10ab (I) and 10bb. The crystal structures of 10ab and 10bb in complex with tubulin confirmed their improved mol. interactions to the colchicine site. In vitro, biol. studies showed that new ABI-231 analogs disrupt tubulin polymerization, promote microtubule fragmentation, and inhibit cancer cell migration. In vivo, analog 10bb not only significantly inhibits primary tumor growth and decreases tumor metastasis in melanoma xenograft models but also shows a significant ability to overcome paclitaxel resistance in a taxane-resistant PC-3/TxR model. In addition, pharmacol. screening suggested that 10bb has a low risk of potential off-target function.

Journal of Medicinal Chemistry published new progress about Antiproliferative agents. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application of C10H9NO.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Lu, Lin; Zheng, Zuoliang; Yang, Yongjie; Liu, Bo; Yin, Biaolin published the artcile< Access to Polycyclic Indol(en)ines via Base-Catalyzed Intramolecular Dearomatizing 3-Alkenylation of Alkynyl Indoles>, Related Products of 4771-48-6, the main research area is indolylmethylpropynamide sodium methoxide catalyst diastereoselective regioselective dearomatization alkenylation spirocyclization; methylidene spiroindolepyrrolidinone preparation; methylidenyl dihydrospiroindolepyrrolidinone preparation; carbamoyl indolylmethylpropynamide sodium methoxide catalyst dearomatization alkenylation cyclization; tetrahydropyrrolopyrroloindole dione preparation diastereoselective regioselective.

Polycyclic indolines and indolenines were synthesized via base-catalyzed intramol. dearomatizing 3-alkenylation reactions of alkynyl indoles at room temperature The base enhanced the nucleophilicity of the carbon at the 3-position of the indole moiety, facilitating an exclusive 5-exo-dig cyclization reaction with the alkyne to form spiroindolenines I, III [R3 = Et, Pr, iso-Pr, etc]. The imine functionality of spiroindolenines I was undergo in-situ nucleophilic addition to form spiroindolines II [R1 = H, 4-Me, 5-Cl, etc.; R2 = Ph, 2-methylphenyl, 3-methylphenyl; R3 = Pr, benzyl, 4-methoxyphenyl; R4 = tert-Bu, cyclohexyl] when R was a carbamoyl group or reduction to form spiroindolines III when R was H.

Chinese Journal of Chemistry published new progress about Alkenes Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Related Products of 4771-48-6.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Qing-Dong; Zhou, Bin; Yang, Jin-Ming; Fang, Dong; Ren, Jiangmeng; Zeng, Bu-Bing published the artcile< Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air>, Related Products of 4771-48-6, the main research area is formylindole preparation green chem regioselective; indole formaldehyde formylation iron catalyst.

An efficient iron-catalyzed C3-selective formylation of free (N-H) or N-substituted indoles such as 2-phenyl-1H-indole, 6-fluoro-1H-indole, 1-methyl-1H-indole, etc. was developed by employing formaldehyde and aqueous ammonia, with air as the oxidant. This new method gave 3-formylindoles such as 2-phenyl-1H-indole-3-carbaldehyde, 6-fluoro-1H-indole-3-carbaldehyde, 1-methyl-1H-indole-3-carbaldehyde, etc. in moderate to excellent yields with fairly short reaction times. Moreover, this procedure for catalytic formylation of indoles can be applied to gram-scale syntheses.

Synlett published new progress about Formylation, regioselective. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Related Products of 4771-48-6.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Chen, Weiliang; Xia, Yong; Lin, Lili; Yuan, Xiao; Guo, Songsong; Liu, Xiaohua; Feng, Xiaoming published the artcile< Asymmetric Synthesis of Furo[3,4-b]indoles by Catalytic [3+2] Cycloaddition of Indoles with Epoxides>, Application In Synthesis of 4771-48-6, the main research area is indole furan furoindole preparation; N,N′-dioxide-metal complex; asymmetric synthesis; epoxides; indoles.

A highly efficient N,N’-dioxide-nickel(II) catalyst system for the catalytic [3+2] cycloaddition of indoles with epoxides through C-C cleavage of oxiranes (i.e., epoxides) was accomplished under mild conditions. It provided a promising approach for chiral furo[3,4-b]indoles in up to 98% yield with up to 91% enantiomeric excess (ee) and >95:5 diastereomeric ratio (d.r.). Under optimized conditions the synthesis of the target compounds was achieved using (1R,1’R,2S,2’S)-1,1′-(1,3-propanediyl)bis[N-[2,4,6-tris(1-methylethyl)phenyl]-2-pyrrolidinecarboxamide] 1,1′-dioxide, perchloric acid nickel(2+) salt hexahydrate (nickel perchlorate hexahydrate) and 1,1,1-trifluoro-N-[(trifluoromethyl)sulfonyl]methanesulfonamide lithium salt (lithium triflimide) as ligand-catalyst combination. Starting materials included 3-(4-methylphenyl)-2,2-oxiranedicarboxylic acid di-Me ester and 1,3-dimethyl-1H-indole derivatives The title compounds thus formed included 1,3a,4,8b-tetrahydro-4,8b-dimethyl-1-(4-methylphenyl)-3H-furo[3,4-b]indole-3,3-dicarboxylic acid 3,3-di-Me ester and related substances.

Chemistry – A European Journal published new progress about [3+2] Cycloaddition reaction. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application In Synthesis of 4771-48-6.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Bai, Jian-Fei; Zhao, Lulu; Wang, Fang; Yan, Fachao; Kano, Taichi; Maruoka, Keiji; Li, Yuehui published the artcile< Organocatalytic Formal (3+2) Cycloaddition toward Chiral Pyrrolo[1,2-a]indoles via Dynamic Kinetic Resolution of Allene Intermediates>, Recommanded Product: 4-Methyl-1H-indole-3-carbaldehyde, the main research area is indole propargylic alc preparation phosphoric acid enantioselective regioselective cycloaddition; pyrroloindole preparation.

The chiral phosphoric acid catalyzed formal (3+2) cycloaddition of 3-substituted 1H-indoles and propargylic alcs. containing a functional directing group (p-NHAc or p-OH) was reported. A straightforward method to synthesize chiral pyrrolo[1,2-a]indole bearing a tetrasubstituted carbon stereocenter was represented. The reaction proceeded smoothly with a wide array of substrate tolerance to deliver various chiral pyrrolo[1,2-a]indoles in up to 93% yield and 98% ee. The utility of this method is highlighted by the diverse transformations of the products into various indole derivatives

Organic Letters published new progress about [3+2] Cycloaddition reaction catalysts (regioselective, stereoselective). 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Recommanded Product: 4-Methyl-1H-indole-3-carbaldehyde.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Zhao, Yin; Li, Hongfang; Yin, Shan; Wu, Yandan; Ni, Guanghui published the artcile< Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst>, SDS of cas: 4771-48-6, the main research area is formyl indole preparation green chem; indole formylation eosin Y visible light.

A visible-light-mediated C-3 formylation of indole catalyzed by eosin Y has been developed using tetramethylethylenediamine as a carbon source and air as an oxidant. This protocol shows high tolerance to a large quantity of functional groups under mild conditions and provides 3-formylated indoles with good yields. This method is a highly attractive alternative to the approach of traditional formylation.

Synlett published new progress about Formylation. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, SDS of cas: 4771-48-6.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Valdenaire, Anja; Pothier, Julien; Renneberg, Dorte; Riederer, Markus A.; Peter, Oliver; Leroy, Xavier; Gnerre, Carmela; Fretz, Heinz published the artcile< Evolution of novel tricyclic CRTh2 receptor antagonists from a (E)-2-cyano-3-(1H-indol-3-yl)acrylamide scaffold>, Application of C10H9NO, the main research area is CRTh2 receptor antagonist cyanoindolylacrylamide preparation structure activity.

(E)-2-(3-(3-((3-Bromophenyl)amino)-2-cyano-3-oxoprop-1-en-1-yl)-1H-indol-1-yl)acetic acid (1) was discovered in a HTS campaign for CRTh2 receptor antagonists. An SAR around this hit could be established and representatives with interesting activity profiles were obtained. Ring closing tactics to convert this hit series into a novel 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole based CRTh2 receptor antagonist series is presented.

Bioorganic & Medicinal Chemistry Letters published new progress about Biological ion transport, calcium. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Application of C10H9NO.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles

Wang, Xin; Lou, Chenhao; Lv, Leiyang; Li, Zhiping published the artcile< Annulative π-Extension (APEX) of Indoles to Pyrido[1,2-a]indoles Using 4-Oxo Peroxides as C4 Units>, Category: indole-building-block, the main research area is pyridoindole preparation; indole annulative pi extension.

Annulative π-extension (APEX) of 3-substituted indoles to pyrido[1,2-a]indoles is developed by using 4-oxo peroxides as π-extending reagents, which are employed as versatile C4 building blocks. This transformation is initiated by Bronsted acid-mediated Hock rearrangement of the peroxyl group. Notably, the pyrido[1,2-a]indole products are obtained by elimination of the indole moiety from the corresponding dihydropyrido[1,2-a]indoles, which could be selectively formed at room temperature

Organic Letters published new progress about Cyclization. 4771-48-6 belongs to class indole-building-block, and the molecular formula is C10H9NO, Category: indole-building-block.

Referemce:
Indole alkaloid derivatives as building blocks of natural products from Bacillus thuringiensis and Bacillus velezensis and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles