November 2022 - Page 56 of 81 - Indole Building Blocks

Chang, Zhe’s team published research in Nature Communications in 2021-12-31 | CAS: 74572-29-5

Nature Communications published new progress about Alkylation. 74572-29-5 belongs to class indole-building-block, name is 5-Chloroisoindolin-1-one, and the molecular formula is C8H6ClNO, Formula: C8H6ClNO.

Chang, Zhe published the artcileCopper catalyzed late-stage C(sp3)-H functionalization of nitrogen heterocycles, Formula: C8H6ClNO, the main research area is functionalized nitrogen heterocycle preparation; nitrogen heterocycle functionalization copper catalyst.

A copper-catalyzed late-stage C(sp3)-H functionalization of N-heterocycles using com. available catalysts under mild reaction conditions was reported. We have investigated eight types of N-heterocycles such as I (R = H, Me) which were usually found in medicinally important skeletons. The scope and utility of this approach were demonstrated by late-stage C(sp3)-H modification of these heterocycles including a number of pharmaceuticals with a broad range of nucleophiles, such as methylation, arylation, azidination, mono-deuteration, and glycoconjugation. Preliminary mechanistic studies revealed that the reaction undergoes a C-H fluorination process which is followed by a nucleophilic substitution.

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

Shultz, Michael D.’s team published research in Journal of Medicinal Chemistry in 2011-07-14 | CAS: 5654-92-2

Journal of Medicinal Chemistry published new progress about Aldehydes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Quality Control of 5654-92-2.

Shultz, Michael D. published the artcileOptimization of the in vitro cardiac safety of hydroxamate-based Histone deacetylase inhibitors, Quality Control of 5654-92-2, the main research area is hydroxamate derivative preparation SAR HDAC inhibotor anticancer.

Histone deacetylase (HDAC) inhibitors have shown promise in treating various forms of cancer. However, many HDAC inhibitors from diverse structural classes have been associated with QT prolongation in humans. Inhibition of the human ether a-go-go related gene (hERG) channel has been associated with QT prolongation and fatal arrhythmias. To determine if the observed cardiac effects of HDAC inhibitors in humans is due to hERG blockade, a highly potent HDAC inhibitor devoid of hERG activity was required. Starting with dacinostat (LAQ824), a highly potent HDAC inhibitor, we explored the SAR to determine the pharmacophores required for HDAC and hERG inhibition. We disclose here the results of these efforts where a high degree of pharmacophore homol. between these two targets was discovered. This similarity prevented traditional strategies for mitigating hERG binding/modulation from being successful and novel approaches for reducing hERG inhibition were required. Using a hERG homol. model, two compounds, I and II, were discovered to be highly efficacious with weak affinity for the hERG and other ion channels.

Varlet, Thomas’s team published research in Journal of the American Chemical Society in 2021-08-04 | CAS: 1009-27-4

Journal of the American Chemical Society published new progress about [4+2] Cycloaddition reaction. 1009-27-4 belongs to class indole-building-block, name is 2-Ethoxy-1H-indole, and the molecular formula is C10H11NO, Recommanded Product: 2-Ethoxy-1H-indole.

Varlet, Thomas published the artcileEnantioselective and Diastereodivergent Synthesis of Spiroindolenines via Chiral Phosphoric Acid-Catalyzed Cycloaddition, Recommanded Product: 2-Ethoxy-1H-indole, the main research area is spiroindolenine preparation diastereoselective enantioselective; indolylmethanol dienecarbamate cycloaddition chiral phosphoric acid catalyst.

A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereogenic centers is achieved by a chiral phosphoric acid-catalyzed cycloaddition of 2-susbtituted 3-indolylmethanols with 1,3-dienecarbamates. Modular access to two different diastereoisomers with high enantioselectivities was obtained by careful choice of reaction conditions. Their functional group manipulation provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles. The origins of this stereocontrol have been identified using DFT calculations, which reveal an unexpected mechanism compared to previous work dealing with enecarbamates.

Zhang, Wen-Qian’s team published research in Organic Letters in 2022-09-16 | CAS: 57663-18-0

Organic Letters published new progress about Benzoyl chlorides Role: RCT (Reactant), RACT (Reactant or Reagent). 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Product Details of C11H11NO2.

Zhang, Wen-Qian published the artcileDearomative Arylcyanation of Indoles via C-CN Bond Activation Enabled by Ni/Lewis Acid Cooperative Catalysis, Product Details of C11H11NO2, the main research area is isoindoloindole carbonitrile preparation stereoselective nickel Lewis acid cooperative catalysis; indolecarbonyl benzonitrile intramol dearomative arylcyanation.

A nickel/Lewis acid cooperatively catalyzed intramol. dearomative arylcyanation of indoles is presented. The reaction proceeds through a C-CN bond activation, dearomatization, and benzylic cyanation sequence, affording 3-cyano fused indolinyl heterocycles in good to excellent yields and excellent diastereoselectivity. The asym. version of the reaction can be established in moderate enantioselectivity by using a chiral ligand.

Yang, Yunhui’s team published research in Chemistry – A European Journal in 2019 | CAS: 41910-64-9

Chemistry – A European Journal published new progress about C-H bond activation. 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Computed Properties of 41910-64-9.

Yang, Yunhui published the artcileRe-Catalyzed Annulations of Weakly Coordinating N-Carbamoyl Indoles/Indolines with Alkynes via C-H/C-N Bond Cleavage, Computed Properties of 41910-64-9, the main research area is pyrroloindolone preparation; alkyne carbamoyl indole annulation rhenium catalyst; pyrroloquinolinone preparation; carbamoyl indolines alkyne annulation rhenium catalyst; C−H activation; annulations; indoles; indolines; rhenium catalysis.

A rhenium-catalyzed [3+2] annulations of N-carbamoyl indoles with alkynes via C-H/C-N bond cleavage, provided rapid access to fused-ring pyrroloindolone derivs I [R1 = H, 6-F, 7-Br, etc.; R2 = R3 = Ph, 4-MeC6H4, 1-naphthyl, etc.]. For the first time, the weakly coordinating O-directing group was successfully employed in rhenium-catalyzed C-H activation reactions, enabled by the unique catalytic ratio of Re2(CO)10, Me2Zn and ZnCl2. Mechanistic studies revealed that aminozinc species played an important role in the reaction. Based on the mechanistic understanding, a more powerful catalytic ratio of Re2(CO)10, [MeZnNPh2]2 and Zn(OTf)2 was devised and applied successfully in the [4+2] annulations of indolines and alkynes affording pyrroloquinolinone derivs II.

Yang, Song’s team published research in Chemical Science in 2018 | CAS: 41910-64-9

Chemical Science published new progress about Bromides Role: RCT (Reactant), RACT (Reactant or Reagent) (α-keto). 41910-64-9 belongs to class indole-building-block, name is 4-Chloroindoline, and the molecular formula is C8H8ClN, Safety of 4-Chloroindoline.

Yang, Song published the artcileRhodium-catalyzed asymmetric hydroamination and hydroindolation of keto-vinylidenecyclopropanes, Safety of 4-Chloroindoline, the main research area is indolinyl tetrahydropyridinol preparation regioselective enantioselective; indoline keto vinylidenecyclopropane hydroamination rhodium catalyst; indolyl tetrahydropyridinol preparation regioselective enantioselective; indole keto vinylidenecyclopropane hydroindolation rhodium catalyst; amino tetrahydropyridinol preparation regioselective enantioselective; secondary amine keto vinylidenecyclopropane hydroamination rhodium catalyst.

A highly regio- and enantioselective hydroamination and hydroindolation of keto-vinylidenecyclopropanes via cationic Rh(I) catalysis was reported in this context. The combination of indolines, various secondary amines and indoles with keto-vinylidenecyclopropanes afforded the corresponding hydrofunctionalization products, e.g., I, II and III resp. in good to excellent yields with outstanding ee values under mild conditions. A new TMM-Rh model complex was proposed, providing an atom economical Rh-π-allyl precursor at the same time. Moreover, the resulting products could easily be transformed into more complex polyheterocycles upon further synthetic manipulation.

Ding, Wei-Yi’s team published research in Chem in 2020-08-06 | CAS: 69622-40-8

Chem published new progress about C-H bond activation. 69622-40-8 belongs to class indole-building-block, name is 2-(tert-Butyl)-5-chloro-1H-indole, and the molecular formula is C12H14ClN, Application of 2-(tert-Butyl)-5-chloro-1H-indole.

Ding, Wei-Yi published the artcileDFT-Guided Phosphoric-Acid-Catalyzed Atroposelective Arene Functionalization of Nitrosonaphthalene, Application of 2-(tert-Butyl)-5-chloro-1H-indole, the main research area is nitrosonaphthalene arene chiral phosphoric acid catalyst enantioselective functionalization.

This strategy enables efficient construction of atropisomeric indole-naphthalenes and indole-anilines with excellent stereocontrol. D. functional theory (DFT) calculations provided further insights into the origins of enantioselectivity and the reaction mechanisms. The successful application in the synthesis of NOBINs (2-amino-2′-hydroxy-1,1′-binaphthyl) extends the utility of this strategy.

Soderberg, Bjorn C. G.’s team published research in Tetrahedron in 2003-10-27 | CAS: 57663-18-0

Tetrahedron published new progress about Cyclization. 57663-18-0 belongs to class indole-building-block, name is Methyl 2-methyl-1H-indole-5-carboxylate, and the molecular formula is C11H11NO2, Synthetic Route of 57663-18-0.

Soderberg, Bjorn C. G. published the artcileIntramolecular cyclization reactions of unsaturated amino Fischer chromium carbenes forming indoles and quinolines, Synthetic Route of 57663-18-0, the main research area is thermally induced intramol annulation alkenylphenylamino substituted Fischer chromium carbene; solvent effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; steric effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; inductive effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; electronic effect intramol annulation alkenylphenylamino substituted Fischer chromium carbene; aminostyrene intramol annulation alkenylphenylamino substituted Fischer chromium carbene; thermal decomposition intramol annulation alkenylphenylamino substituted Fischer chromium carbene; carbonyl alkylidene amino chromium Fischer carbene preparation intramol cyclization; amino carbonyl alkylidene chromium Fischer carbene preparation intramol cyclization; dubamine amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; quinoline amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; quinolinecarboxylic amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; indole amino carbonyl alkylidene chromium Fischer carbene intramol cyclization; indolecarboxylic amino carbonyl alkylidene chromium Fischer carbene intramol cyclization.

A thermally induced intramol. annulation reaction of N-(2-alkenylphenyl)amino substituted Fischer chromium carbenes has been extensively examined The carbene complexes were prepared in moderate to good yields by reaction of 2-aminostyrenes with intermediately formed acyloxy substituted carbenes. Upon heating, the thermally labile carbenes decomposed producing indoles and quinolines as the major products. The product distribution was found to be highly dependent on the substitution pattern and electronic properties of the starting material, and on the solvent used. The reaction of pentacarbonyl[1-[[2-ethenyl-3-(methoxycarbonyl)phenyl]amino]ethylidene]chromium gave 2-methyl-1H-indole-4-carboxylic acid Me ester. The reaction of pentacarbonyl[1-[[2-(1-methylethenyl)phenyl]amino]ethylidene]chromium gave 2,4-dimethylquinoline and 1,2,3,4-tetrahydro-2,4-dimethylquinoline.

Larsen, Matthew A.’s team published research in Journal of the American Chemical Society in 2014-03-19 | CAS: 5654-92-2

Journal of the American Chemical Society published new progress about Borylation (regioselective). 5654-92-2 belongs to class indole-building-block, name is N,N-Dimethyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)methanamine, and the molecular formula is C10H13N3, Product Details of C10H13N3.

Larsen, Matthew A. published the artcileIridium-Catalyzed C-H Borylation of Heteroarenes: Scope, Regioselectivity, Application to Late-Stage Functionalization, and Mechanism, Product Details of C10H13N3, the main research area is iridium catalyzed carbon hydrogen borylation heteroarene regioselectivity functionalization mechanism; tetramethylphenanthroline iridium catalyzed heteroarene borylation regioselectivity computational study.

A study on the iridium-catalyzed C-H borylation of heteroarenes is reported. Several heteroarenes containing multiple heteroatoms were amenable to C-H borylation catalyzed by the combination of an iridium(I) precursor and tetramethylphenanthroline. The investigations of the scope of the reaction led to the development of powerful rules for predicting the regioselectivity of borylation, foremost of which is that borylation occurs distal to nitrogen atoms. One-pot functionalizations are reported of the heteroaryl boronate esters formed in situ, demonstrating the usefulness of the reported methodol. for the synthesis of complex heteroaryl structures. Application of this methodol. to the synthesis and late-stage functionalization of biol. active compounds is also demonstrated. Mechanistic studies show that basic heteroarenes can bind to the catalyst and alter the resting state from the olefin-bound complex observed during arene borylation to a species containing a bound heteroarene, leading to catalyst deactivation. Studies on the origins of the observed regioselectivity show that borylation occurs distal to N-H bonds due to rapid N-H borylation, creating an unfavorable steric environment for borylation adjacent to these bonds. Computational studies and mechanistic studies show that the lack of observable borylation of C-H bonds adjacent to basic nitrogen is not the result of coordination to a bulky Lewis acid prior to C-H activation, but the combination of a higher-energy pathway for the borylation of these bonds relative to other C-H bonds and the instability of the products formed from borylation adjacent to basic nitrogen.

Jin, Jiang’s team published research in Organic & Biomolecular Chemistry in 2021 | CAS: 13523-93-8

Organic & Biomolecular Chemistry published new progress about Crystal structure. 13523-93-8 belongs to class indole-building-block, name is 4-(Benzyloxy)-1-methyl-1H-indole, and the molecular formula is C16H15NO, Formula: C16H15NO.

Jin, Jiang published the artcileSelectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor, Formula: C16H15NO, the main research area is indole MTBE Selectfluor promoter oxidative methylenation green chem; bisindolyl methane preparation; dicarbonyl compound MTBE Selectfluor promoter oxidative methylenation green chem; methylene bis dicarbonyl compound preparation.

A novel, green and efficient method was developed for the synthesis of methylene bridged bis(indolyl)methanes in good to excellent yields. The reaction employed Me tert-Bu ether (MTBE) as the methylene source and Selectfluor as an oxidizing agent. The scope and versatility of the methods was successfully demonstrated with 48 examples. The metal-free transformation process was suitable for scale-up production A Selectfluor-promoted oxidative reaction mechanism was proposed based on the results of the exptl. studies.