Category: 883526-76-9

On March 28, 2011, Masuda, Kohei; Ohmura, Toshimichi; Suginome, Michinori published an article.Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde The title of the article was 2-Vinylindoles As the Four-Atom Component in a Catalytic [4+1] Cycloaddition with a Silylene-Palladium Species Generated from (Aminosilyl)boronic Ester. And the article contained the following:

The palladium-catalyzed silylene transfer to 2-alkenylindoles from a silylboronic ester bearing a diethylamino group on the silicon atom takes place efficiently, resulting in the formation of a 1-sila-3-cyclopentene ring fused with the indole ring. Further silylene transfer proceeds in the reaction of 2-(1-alkenyl)indoles, giving bissilylated tricyclic indoles in high yields. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to vinylindole preparation palladium phosphine catalyzed bissilylative cyclization, indolosilacyclopentene preparation crystal mol structure, catalysis cycloaddition silylene palladium aminosilylboronic ester and other aspects.Safety of 1,5-Dimethyl-1H-indole-2-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

On January 1, 2014, Su, Tao; Han, Xiuling; Lu, Xiyan published an article.HPLC of Formula: 883526-76-9 The title of the article was Palladium(II)-catalyzed oxidative annulation of alkenylindoles with alkynes initiated by C-H activation. And the article contained the following:

In the presence of Pd(OAc)2, indolylalkenyl carbonyl compounds such as I (R = H, Me, Cl; R1 = Me, PhCH2; R2 = MeCO, PhCO, 4-MeOC6H4CO, 4-MeC6H4CO, t-BuCO, NC, EtO2C) underwent Cu(OAc)2-mediated oxidative cycloaddition with diarylalkynes R3CCR3 (R3 = Ph, 4-MeC6H4, 4-FC6H4, 4-ClC6H4) to give alkylidenediarylcyclopentindoles such as II in 42-99% yields as mixtures of diastereomers (for II) or as single diastereomers (for 1-alkylidene-2,3-diarylcyclopentindoles). The structures of II (R = H; R1 = Me; R2 = PhCO, EtO2C; R3 = Ph) and of a (benzoylmethylene)diphenylcyclopentindole were determined by X-ray crystallog. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).HPLC of Formula: 883526-76-9

The Article related to alkylidenediarylcyclopentindole preparation, indolylalkenyl carbonyl compound stereoselective preparation, chemoselective oxidative cycloaddition arylalkyne indolylalkenyl carbonyl compound palladium catalyst and other aspects.HPLC of Formula: 883526-76-9

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

On October 15, 2018, Uredi, Dilipkumar; Motati, Damoder Reddy; Watkins, E. Blake published an article.Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde The title of the article was A Unified Strategy for the Synthesis of β-Carbolines, γ-Carbolines, and Other Fused Azaheteroaromatics under Mild, Metal-Free Conditions. And the article contained the following:

An efficient, unified approach for the synthesis of β-carbolines, γ-carbolines, and other fused azaheteroaroms. has been realized under metal-free conditions, from propargylic amines and (hetero)aromatic aldehydes. This unified strategy provides β- and γ-carbolines as well as a range of fused azaheteroaroms. with a broad substrate scope and excellent functional group compatibility. The formal synthesis of oxopropalines D and G has been achieved on gram scale using I, in a one-pot reaction from com. available materials (previous shortest reported route to I was 5 steps). NMR studies of the conversion of imine intermediate II to β-carboline I were conducted and revealed that the reaction proceeded through an allene intermediate. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to propargylic amine heteroaromatic aldehyde isomerization azacyclization proton shift, carboline preparation metal free, fused azaheteroarom preparation, oxopropalines d formal synthesis, formal synthesis oxopropalines g and other aspects.Recommanded Product: 1,5-Dimethyl-1H-indole-2-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

On June 2, 2017, Li, Long; Chen, Xiu-Mei; Wang, Ze-Shu; Zhou, Bo; Liu, Xin; Lu, Xin; Ye, Long-Wu published an article.Category: indole-building-block The title of the article was Reversal of Regioselectivity in Catalytic Arene-Ynamide Cyclization: Direct Synthesis of Valuable Azepino[4,5-b]indoles and β-Carbolines and DFT Calculations. And the article contained the following:

Ynamides are important building blocks in organic synthesis, and a variety of versatile synthetic methods have been developed in the past decade. Among these, catalytic cyclizations of π-tethered ynamides are particularly attractive, since this approach enables facile access to a diverse array of synthetically useful nitrogen heterocycles. However, due to the fact that the nitrogen atom is able to impose an electronic bias, these cyclizations exclusively occur on the α position of ynamides. Herein, we report the reversal of regioselectivity in arene-ynamide cyclization by copper catalysis, which represents the first catalytic π-tethered ynamide cyclization involving the reversal of regioselectivity. This strategy allows the expedient and practical synthesis of valuable azepino[4,5-b]indoles and β-carbolines in generally high yields under mild conditions. Moreover, the relevant mechanistic rationale for this cyclization, especially for the observed high regioselectivity, is strongly supported by d. functional theory (DFT) calculations The synthetic utility of this chem. is also indicated by the synthesis of several biol. active compounds and natural product bauerine A. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Category: indole-building-block

The Article related to crystal mol structure azepino indole carboline, carboline preparation regioselective reversal catalytic tethered ynamide cyclization, azepino indole preparation regioselective reversal catalytic tethered ynamide cyclization and other aspects.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

Wani, Imtiyaz Ahmad; Bhattacharyya, Aditya; Sayyad, Masthanvali; Ghorai, Manas K. published an article in 2018, the title of the article was Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles.Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

Direct and expedient access to densely substituted tetrahydrocarbazoles I [R1 = H, F; R2 = H, Me, CH2CH:CH2; R3 = OMe, OEt, Ph] and tetrahydrocycloheptadiindoles bearing multiple contiguous stereocenteres II [R1 = H, F, Cl, Me] were achieved via a two-fold divergent diastereoselective (dr up to >99:1) transformation of 2-vinylindoles. The high-yielding conversions (yield up to 87%) that were amenable for a wide range of substituted 2-vinylindoles proceeded through Lewis acid-catalyzed [4 + 2] and [4 + 3] cyclization-aromatization cascade reactions, resp., involving a heretofore-unprecedented reversal of the polarity (umpolung) of 2-vinylindoles. The two synthetic routes were effortlessly transposable into each other by merely modulating the temperature to furnished the corresponding products in a selective and exclusive fashion. In addition, another novel synthetic route to tetrahydroindolocarbazoles was developed that advances via a formal [4+2] cyclization of 4-vinylindoles involving sequential C3 Michael addition-dearomatization-aromatization cascade reactions. Diastereo- and chemoselective preparation of tetrahydrocarbazoles and tetrahydrocycloheptadiindoles via Fe(OTf)3 catalyzed tandem cyclization-aromatization of vinylindoles. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Application In Synthesis of 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to tetrahydrocarbazole preparation diastereoselective chemoselective, tetrahydrocycloheptadiindole preparation diastereoselective chemoselective, vinylindole iron trifluoromethanesulfonate catalyst tandem cyclization aromatization and other aspects.Application In Synthesis of 1,5-Dimethyl-1H-indole-2-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

Bandini, Marco; Gualandi, Andrea; Monari, Magda; Romaniello, Alessandro; Savoia, Diego; Tragni, Michele published an article in 2010, the title of the article was Allylic alcohols: Valuable synthetic equivalents of non-activated alkenes in gold-catalyzed enantioselective alkylation of indoles.SDS of cas: 883526-76-9 And the article contains the following content:

The recent booming of gold catalysis has demonstrated that unprecedented transformations can be realized in a highly selective manner. Moreover, due to the growing availability of chiral organic ligands, gold-catalysis can be considered as one of most dynamic hot spots in asym. synthesis. However, in this context, the use of non-activated olefinic C-C double bonds is still largely unexplored due to the intrinsic inertness of C=C (respect to allenes and alkynes) in taking part in nucleophilic additions assisted by π-electrophilic activations. Allylic alcs. have been demonstrated to be feasible “surrogates” of non-activated alkenes for the enantioselective allylic alkylation of indoles catalyzed by chiral gold(I) complexes. In this investigation, a full account addressing efficiency and substrate scope of such a process is presented. The products, tetrahydrocarbazoles or tetrahydro-β-carbolines, are obtained in moderate to good yields and 40-86% ee from the corresponding Z-allylic alc.-containing substrates, while the E isomers are unreactive. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).SDS of cas: 883526-76-9

The Article related to allylic alc tethered indole derivative preparation, chiral ligand gold catalyzed intramol allylic alkylation indole derivative, tetrahydrocarbazole derivative stereoselective preparation, tetrahydrocarboline derivative stereoselective preparation and other aspects.SDS of cas: 883526-76-9

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

Galvan, Alicia; Calleja, Jonas; Gonzalez-Perez, Adan B.; Alvarez, Rosana; de Lera, Angel R.; Fananas, Francisco J.; Rodriguez, Felix published an article in 2015, the title of the article was Stereoselective [3+2] Carbocyclization of Indole-Derived Imines and Electron-Rich Alkenes: A Divergent Synthesis of Cyclopenta[b]indole or Tetrahydroquinoline Derivatives.Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

An unprecedented stereoselective [3+2] carbocyclization reaction of indole-2-carboxaldehydes, anilines, and electron-rich alkenes to obtain cyclopenta[b]indoles is disclosed. This pathway is different from the well-established Povarov reaction: the formal [4+2] cycloaddition involving the same components, which affords tetrahydroquinolines. Moreover, by simply changing the Bronsted acid catalyst, this multicomponent coupling process could be divergently directed towards the conventional Povarov pathway to produce tetrahydroquinolines or to the new pathway (anti-Povarov) to generate cyclopenta[b]indoles. Supported by computational studies, a stepwise Mannich/Friedel-Crafts cascade is proposed for the new anti-Povarov reaction, whereas a concerted [4+2] cycloaddition mechanism is proposed for the Povarov reaction. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Name: 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to cyclopentaindole derivative stereoselective preparation, tetrahydroquinoline derivative stereoselective preparation, indolecarboxaldehyde arylamine dihydrofuran stereoselective carbocyclization, acid catalysis, divergent synthesis, heterocycles, indoles, synthetic methods and other aspects.Name: 1,5-Dimethyl-1H-indole-2-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

On February 16, 2018, Kong, Xiang-Fei; Zhan, Feng; He, Guo-Xue; Pan, Cheng-Xue; Gu, Chen-Xi; Lu, Ke; Mo, Dong-Liang; Su, Gui-Fa published an article.HPLC of Formula: 883526-76-9 The title of the article was Gold-Catalyzed Selective 6-exo-dig and 7-endo-dig Cyclizations of Alkyne-Tethered Indoles To Prepare Rutaecarpine Derivatives. And the article contained the following:

An efficient method to synthesize rutaecarpine derivatives I [R1 = H, OMe-3, Me-3, Cl-3, Br-3, I-3, F-2, Cl-4; R2 = Me, CH2Ph, H; R3 = Me-10, Br-10, Cl-11; R4 = H, Me, SiMe3] and II [R1 = H, OMe, Cl, Br, I; R3 = H, Cl; R4 = H, Me, Ph, SiMe3] via the gold-catalyzed selective cyclization of alkyne-tethered indoles III under mild conditions is described. The alkyne-tethered indole can undergo 6-exo-dig cyclization by oxidation and sequential gold catalysis, while it goes through 7-endo-dig cyclization by gold catalysis and sequential oxidation Substrate scope studies reveal that the selectivity of cyclization was controlled by the substrates with sp3 and sp2 hybridization of carbon at the 2 position in quinazolinone. Furthermore, the rutaecarpine scaffold was prepared in 67% yield at gram scale easily in four steps from isatoic anhydride. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).HPLC of Formula: 883526-76-9

The Article related to rutaecarpine alkaloid derivative scaffold preparation, quinazolinone alkyne tethered indoles gold catalyzed selective cyclization, exo dig cyclization gold catalysis quinazolinone alkyne tethered indoles, endo dig cyclization gold catalysis quinazolinone alkyne tethered indoles and other aspects.HPLC of Formula: 883526-76-9

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

Li, Long; Zhou, Bo; Wang, Yong-Heng; Shu, Chao; Pan, Yi-Fei; Lu, Xin; Ye, Long-Wu published an article in 2015, the title of the article was Zinc-Catalyzed Alkyne Oxidation/C-H Functionalization: Highly Site-Selective Synthesis of Versatile Isoquinolones and β-Carbolines.Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde And the article contains the following content:

An efficient zinc(II)-catalyzed alkyne oxidation/C-H functionalization sequence was developed, leading to a highly site-selective synthesis of a variety of isoquinolones, e.g., I, and β-carbolines, e.g., II. Importantly, in contrast to the well-established gold-catalyzed intermol. alkyne oxidation, over-oxidation was completely suppressed in this system and the reaction most likely proceeds by a Friedel-Crafts-type pathway. Mechanistic studies and theor. calculations were described. The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).Recommanded Product: 1,5-Dimethyl-1H-indole-2-carbaldehyde

The Article related to ynamide benzyl alkyne oxidation regioselective functionalization zinc triflate, indolylmethyl ynamide alkyne oxidation regioselective functionalization zinc triflate, isoquinolone preparation, carboline beta preparation, heterocycles, homogeneous catalysis, nitrogen oxides, synthetic methods, zinc and other aspects.Recommanded Product: 1,5-Dimethyl-1H-indole-2-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

On January 1, 2018, He, Yi; Li, Zhenghua; Robeyns, Koen; Van Meervelt, Luc; Van der Eycken, Erik V. published an article.HPLC of Formula: 883526-76-9 The title of the article was A Gold-Catalyzed Domino Cyclization Enabling Rapid Construction of Diverse Polyheterocyclic Frameworks. And the article contained the following:

We report herein an efficient gold(I)-catalyzed post-Ugi domino dearomatization/ipso-cyclization/Michael sequence that enables access to libraries of diverse (hetero)arene-annulated tricyclic heterocycles. This process affords novel complex polycyclic scaffolds in moderate to good yields from readily available acyclic precursors with excellent chemo-, regio-, and diastereoselectivity. The power of this strategy has been demonstrated by the rapid synthesis of 40 highly functionalized polyheterocycles bearing indole, pyrrole, (benzo)furan, (benzo)thiophene, pyrazole, and electron-rich arene groups in two operational steps. Thus, e.g., treatment of Ugi adduct I with IPrAuCl/AgOTf afforded polyheterocycle II (96%). The experimental process involved the reaction of 1,5-Dimethyl-1H-indole-2-carbaldehyde(cas: 883526-76-9).HPLC of Formula: 883526-76-9

The Article related to gold catalyzed domino cyclization diverse polyheterocyclic compound synthesis, chemoselective synthesis polyheterocyclic compound, regioselective synthesis polyheterocyclic compound, diastereoselective synthesis polyheterocyclic compound, ugi reaction, dearomatization, domino cyclization, gold catalysis, heterocycles and other aspects.HPLC of Formula: 883526-76-9

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