Category: indole-building-block

On June 30, 2006, Qian, Chao; Zhang, Jia-sen; Liu, Jian-qing; Li, Lu-zhen; Chen, Xin-zhi published an article.Reference of H-Idc-OH The title of the article was Study on the synthesis of S-(-)-2-Carboxyindoline. And the article contained the following:

A general synthetic route of S-(-)-2-carboxyindoline was proposed which started from o-nitrotoluene and di-Et oxalate, via condensation, nitro-group reduction, heterocyclic reduction and hydrolysis, 2-carboxyindoline was achieved with total yield of 40.6%. Especially, using 10% Pd-C as catalysts, the heterocycle is reduced easily with hydrogen at 160° and 6.2 MPa, the catalysts also can be reclaimed. Through steps of chlorination, esterification, fractional crystallization, and hydrolysis, the S-(-)-2-carboxyindoline was resolved with L-carnitine oxalate as the chiral resolution reagent. The titled product can be achieved with 32% yield and [α20589 = -27.5] (c = 1.0, DMSO). The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Reference of H-Idc-OH

The Article related to carboxyindoline preparation nitrotoluene chiral resolution carnitine oxalate, Industrial Organic Chemicals, Leather, Fats, and Waxes: Manufacture Of Industrial Organic Chemicals and other aspects.Reference of H-Idc-OH

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 March 15, 2011, Ali, Ashif Md.; Punniyamurthy, Tharmalingam published an article.Safety of Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Domino ligand-free copper-catalyzed synthesis of polysubstituted indoles. And the article contained the following:

The synthesis of polysubstituted indoles is described by the domino reaction of 2-haloanilines and 1,3-dicarbonyl compounds, 1,3-diketones, β-keto esters and β-keto amides, using copper catalysis under ligand-free conditions. The protocol provides a simple, general and atom economical process for the synthesis of substituted indoles at moderate temperature The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Safety of Methyl 2-methyl-1H-indole-3-carboxylate

The Article related to indole preparation, haloaniline dicarbonyl compound cyclocondensation copper, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Safety of Methyl 2-methyl-1H-indole-3-carboxylate

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

Basolo, Luca; Bernasconi, Alice; Borsini, Elena; Broggini, Gianluigi; Beccalli, Egle M. published an article in 2011, the title of the article was Solvent-Free, Microwave-Assisted N-Arylation of Indolines by using Low Palladium Catalyst Loadings.Recommanded Product: 79815-20-6 And the article contains the following content:

A series of substituted N-arylindolines is prepared by a solvent-free, palladium-catalyzed procedure. The procedure requires only low loadings of catalyst, uses microwave irradiation, and starts from com. available substrates. The method proceeds in good yields and in short reaction times with aryl bromides, chlorides, and iodides, also on 2-substituted indolines. The combination of solvent-free methods with microwave heating will further increase in importance in the search for more environmentally acceptable synthesis methods. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Recommanded Product: 79815-20-6

The Article related to indoline aryl preparation aryl halide palladium phosphine catalyst microwave, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Recommanded Product: 79815-20-6

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

On February 28, 2011, de Lange, Ben; Hyett, David J.; Maas, Peter J. D.; Mink, Daniel; van Assema, Friso B. J.; Sereinig, Natascha; de Vries, Andre H. M.; de Vries, Johannes G. published an article.Synthetic Route of 79815-20-6 The title of the article was Asymmetric Synthesis of (S)-2-Indolinecarboxylic Acid by Combining Biocatalysis and Homogeneous Catalysis. And the article contained the following:

The use of a combination of biocatalysis and homogeneous catalysis led to a very short synthesis route to enantiopure (S)-2-indolinecarboxylic acid. Thus, reacting 2-ClC6H4CHO with Ac2O/NaOAc gave 2-ClC6H4CH:CHCO2H in 55% yield. The latter compound was treated with phenylalanine ammonia lyase to give (S)-2-ClC6H4CH2CH(NH2)CO2H (I), that, upon addition of CuCl/H2O, produced 77% of the title compound Alternatively, treating 2-ClC6H4CH:CH(NHCOMe)CO2H with [Rh(cod)2]BF4/MonoPhos/H2CH2Cl2 gave the reduced compound which was then converted into I and taken on to the final compound as stated above. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Synthetic Route of 79815-20-6

The Article related to indolinecarboxylic acid asym synthesis biocatalysis homogeneous catalysis, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Synthetic Route of 79815-20-6

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

On April 28, 2010, Guan, Zheng-Hui; Yan, Ze-Yi; Ren, Zhi-Hui; Liu, Xue-Yuan; Liang, Yong-Min published an article.Synthetic Route of 65417-22-3 The title of the article was Preparation of indoles via iron catalyzed direct oxidative coupling. And the article contained the following:

Iron-catalyzed aryl C-H and vinyl C-H bonds activation to give valuable substituted indole products, e.g. I, from 3-(phenylamino)but-2-enoates, e.g. II, was reported. The reaction shows high functional group tolerance. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Synthetic Route of 65417-22-3

The Article related to indole preparation, phenylaminobutenoate oxidative coupling iron catalyst, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Synthetic Route of 65417-22-3

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 4, 2016, Liu, Xiao-Guang; Li, Zi-Hao; Xie, Jian-Wei; Liu, Ping; Zhang, Jie; Dai, Bin published an article.Product Details of 65417-22-3 The title of the article was Copper-catalyzed synthesis of 2,3-disubstituted indoles from ortho-haloanilines and β-keto esters/β-diketone. And the article contained the following:

Tetrazole-1-acetic acid was identified as an efficient ligand to promote copper-catalyzed domino reaction of ortho-iodo/bromo-anilines RNH2 (R = 2-IC6H4, 2-I-5-H3CC6H3, 3-iodopyridin-2-yl, 2,4-Br2C6H3, etc.) with β-keto esters/β-diketone R1C(O)CH2C(O)R2 (R1 = CH3, (CH3)CH, C6H5, etc.; R2 = CH3, CH2CH3, OCH3, OCH2CH3) for 2,3-disubstituted indoles’ synthesis, e.g., I, with high yields under mild conditions. The protocol, with an easily-available catalytic system, shows good substrate tolerance towards various functional groups. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Product Details of 65417-22-3

The Article related to indole preparation, ortho haloaniline dicarbonyl compound domino reaction copper catalyst, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Product Details of 65417-22-3

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 March 31, 2013, Liu, Jin-Qiang; Chen, Xin-Zhi; Ji, Baoming; Zhao, Bang-Tun published an article.Application of 79815-20-6 The title of the article was Transformation of L-phenylalanine to (S)-indoline-2-carboxylic acid without group-protection. And the article contained the following:

(S)-Indoline-2-carboxylic acid was synthesized by use of a nitro amination approach with L-phenylalanine as chiral pool. The first step of the synthesis was nitration of L-phenylalanine, with urea nitrate (UN)/H2SO4 as nitrating reagent, to give 2,4-dinitro-L-phenylalanine in 75.7 % yield in one-pot synthesis and 69.1 % yield by step-wise nitration. Intramol. nitro amination of 2,4-dinitro-L-phenylalanine gave (S)-6-nitro-indoline-2-carboxylic acid in 65.7 % yield and more than 99.5 % enantiomeric excess (ee). The title compound, (S)-indoline-2-carboxylic acid, was obtained in 85.9 % yield and high ee by one-pot transformation of (S)-6-nitroindoline-2-carboxylic acid. The total synthesis consisted of three operations and gave the title compound in 42 % yield and more than 99.5 % ee. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application of 79815-20-6

The Article related to phenylalanine transformation indoline carboxylic acid preparation protection group free, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Application of 79815-20-6

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

On March 31, 1986, Pindur, Ulf; Flo, Camran published an article.Name: Methyl 2-methyl-1H-indole-3-carboxylate The title of the article was Reactions of electron-rich heterocycles with derivatives of carboxylic ortho acids. VII. Regioselective, mild acylation of 2-methylindole with di- and trialkoxycarbenium tetrafluoroborates. A simple procedure for deriving 3-acyl-2-methylindoles and 3-methoxycarbonyl-2-methylindole. And the article contained the following:

The regioselective acylation of 2-methylindole with RC+(OR1)2BF4- (R = H, Me, R1 = Et; R = Ph, R1 = Me; R = OMe, R1 = Me) gave indoles I [R2 = MeCOPhCO,CO2Me). The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Name: Methyl 2-methyl-1H-indole-3-carboxylate

The Article related to methylindole acylation alkoxycarbenium tetrafluoroborate regiochem, indole acyl carboxy, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Name: Methyl 2-methyl-1H-indole-3-carboxylate

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 6, 1996, Hashimoto, Rie; Okada, Hideo; Mochizuki, Atsuya; Ooi, Hideo; Endo, Mamoru; Miki, Wataru; Konya, Kazumi published a patent.Computed Properties of 52537-00-5 The title of the patent was Preparation of 5,6-dichloro-1-methylgramine and antifouling agents against adhering aquatic organisms. And the patent contained the following:

The title compound (I) is prepared An antifouling agent against adhering aquatic organisms contains at least one compound selected from 5,6-dichlorogramine, 5-chloro-2-methylgramine, 5-bromo-2-methylgramine, 1,2-dimethyl-6-bromogramine, and I as the active ingredient. This antifouling agent prevents aquatic organisms such as sea weeds, barnacles, Mytilus edulis, etc. adhering and damaging a bottom of a ship, a fishing net, a buoy, aqueous structures such as facilities attached to a dam and bay, and water inlet channels for cooling water of a condenser for a power plant or an heat exchanger in petrochem. industry. Thus, 1.9 g 5,6-dichloroindole was dissolved in DMF, treated with NaH at 5°, stirred at 5° for 30 min, treated dropwise with 1.5 g MeI, and stirred at room temperature for 3 h to give 2.2. g crude 5,6-dichloro-1-methylindole, which was added to a solution of 1.3 mL 40% dimethylamine, 0.9 mL 35% formalin, and 1.7 mL AcOH, and stirred overnight to give 61.5% I. I (0.0025 mg) was dissolved in 0.1 mL MeOH, coated on a round petri dish (diameter 4 cm), and dried. Filtered sea water (5 mL) and 10 barnacle larvae were added to the treated petri dish and left in the dark at 23° for 24 h to show that no larvae adhered to the petri dish. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Computed Properties of 52537-00-5

The Article related to chloromethylgramine preparation antifouling agent, aquatic organism antifouling agent, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Computed Properties of 52537-00-5

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 March 3, 2017, Jiang, Xue; Tang, Weijun; Xue, Dong; Xiao, Jianliang; Wang, Chao published an article.Synthetic Route of 52537-00-5 The title of the article was Divergent Dehydrogenative Coupling of Indolines with Alcohols. And the article contained the following:

The dehydrogenative coupling of indolines with alcs. catalyzed by an iridium complex has been achieved to afford both N- and C3-alkylated indoles selectively, by simply changing the addition time of a base additive. The iridacycle catalyst plays multiple roles in these reactions, which dehydrogenates both amines and alcs. and catalyzes the coupling reactions. Mechanistic studies reveal that a borrowing hydrogen-dehydrogenation process and a dehydrogenation-borrowing hydrogen process are involved in N-alkylation and C3-alkylation reactions, resp. The C3-alkylation reaction involves the direct coupling of two sp3 carbon centers. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Synthetic Route of 52537-00-5

The Article related to iridium catalyst dehydrogenative coupling indoline alc, indole alkylated preparation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Synthetic Route of 52537-00-5

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