Category: indole-building-block

On March 26, 2007, Chen, Yihui; Shibata, Masayuki; Rajeswaran, Manju; Srikrishnan, Thamarapu; Dugar, Sundeep; Pandey, Ravindra K. published an article.HPLC of Formula: 256935-86-1 The title of the article was Utility of Japp-Klingemann reaction for the preparation of 5-carboxy-6-chloroindole via Fischer indole protocol. And the article contained the following:

5-Carboxy-6-chloroindole, a precursor for p38 kinase inhibitor, was prepared from 4-amino-2-chloro-3-iodobenzoic acid by following the Japp-Klingemann synthetic approach. The structures of the key intermediates were also confirmed by X-ray analyses. Computational anal. was helpful in understanding the importance of the substituents at the cyclization step of the synthesis. The experimental process involved the reaction of 6-Chloro-1H-indole-5-carboxylic acid(cas: 256935-86-1).HPLC of Formula: 256935-86-1

The Article related to carboxychloroindole preparation japp klingemann reaction, indolecarboxylic acid chloro preparation japp klingemann reaction, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.HPLC of Formula: 256935-86-1

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 11, 2017, Liu, Huan; Chen, Jian-Gang; Wang, Chao; Liu, Zhao-Tie; Li, Yang; Liu, Zhong-Wen; Xiao, Jianliang; Lu, Jian published an article.Product Details of 52537-00-5 The title of the article was Immobilization of Cyclometalated Iridium Complex onto Multiwalled Carbon Nanotubes for Dehydrogenation of Indolines in Aqueous Solution. And the article contained the following:

Increasing concerns about the potentially neg. impacts of chem. production on sustainable development of the overall environment have spurred numerous attempts to seek greener reaction mediums, recyclable catalysts, and high-efficiency procedures. Herein, a cyclometalated Ir complex with a pyrene tag was successfully immobilized onto multiwalled carbon nanotubes via π-π stacking interactions, through which an easily reusable Ir catalyst was constructed. The immobilization process was effectively monitored by using a fluorescence spectroscopy technique, and the immobilized Ir catalyst was well characterized and evaluated. It is found that the immobilized Ir catalyst exerts activity comparable to that of the corresponding homogeneous Ir catalyst for the dehydrogenation of indolines in an aqueous solution More importantly, the catalyst could be recycled seven times without obvious loss of the Ir-active center and noticeable decrease in the yield of the targeted product. Addnl., the observed slight deactivation of the catalyst during the recycle is also discussed. The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Product Details of 52537-00-5

The Article related to indoline cyclometalated carbon nanotube immobilized iridium complex dehydrogenation catalyst, indole preparation green chem, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Product Details 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

Wender, Paul A.; Cooper, Christopher B. published an article in 1986, the title of the article was The photochemistry of 1-alkenylbenzotriazoles. Methodology for the synthesis of indoles.Related Products of 65417-22-3 And the article contains the following content:

Indoles I [R = (CH2)3OSiMe2CMe3, R1 = H; R = H, R1 = (CH2)3OSiMe2CMe3; R = Me, R1 = CO2Me; RR1 = (CH2)3, (CH2)4] were prepared by photolysis of 1-alkenylbenzotriazoles II. The 2,3-dihydropyrrolo[1,2-a]indole nucleus of the mitomycin antitumor antibiotics was prepared by desilylating I [R = (CH2)3OSiMe2CMe3, R1 = H], tosylating the alc., and ring closure of the tosylate. The experimental process involved the reaction of Methyl 2-methyl-1H-indole-3-carboxylate(cas: 65417-22-3).Related Products of 65417-22-3

The Article related to indole, pyrroloindole mitomycin preparation, alkenylbenzotriazole preparation photolysis, benzotriazole alkenyl photolysis, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Related Products 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

Wang, Guo-Peng; Chen, Meng-Qing; Zhu, Shou-Fei; Zhou, Qi-Lin published an article in 2017, the title of the article was Enantioselective Nazarov cyclization of indole enones cooperatively catalyzed by Lewis acids and chiral Bronsted acids.SDS of cas: 883526-76-9 And the article contains the following content:

The use of cooperative catalysis using Lewis acids and chiral Bronsted acids to control the stereochem. of the tertiary α-carbon I (R = H, 7-Me, 7-F, 7-Cl, 8-F; R1 = Me, Ph, 2H-1,3-benzodioxol-5-yl, etc.) in the products of this reaction has been reported. Specifically, with ZnCl2 and a chiral spiro phosphoric acid as catalysts, the first enantioselective construction of cyclopenta[b]indoles with chiral tertiary α-carbons I was realized via Nazarov cyclization of indole enone substrates II (R2 = H, 5-Me, 5-F, 5-Cl, 4-F) with only one coordinating site. Mechanistic studies revealed that the chiral spiro phosphoric acid acts as a multifunctional catalyst and it co-catalyzes the cyclization of the dienone and enantioselectively catalyzes a proton transfer reaction of the enol intermediate. This new strategy of enantioselective control by means of cooperative catalysis may show utility for other challenging asym. cyclization reactions. 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 cyclopentaindole preparation enantioselective, indole enone nazarov cyclization lewis acid chiral phosphoricacid catalyst, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles 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

On December 30, 2004, Howlett, Anthony R.; Rice, Audie; Moshinsky, Deborah; Hammarsten, Ola published a patent.Electric Literature of 52537-00-5 The title of the patent was A preparation of sulfonamide substituted indolinones, useful as inhibitors of DNA dependent protein kinase (DNA-PK). And the patent contained the following:

The invention relates to a preparation of sulfonamide substituted indolinones of formula I [wherein: R1 and R2 are independently selected from H, (un)substituted Ph, thiazolyl, or alkyl, etc.; R3, R4, and R5 are independently selected from H or alkyl], useful as inhibitors of DNA dependent protein kinase (DNA-PK). The invention relates to the field of radiosensitizing agents which are capable of enhancing radiotherapy by inhibiting DNA-PK (DNA-protein kinase). For instance, sulfonamide substituted indolinone II was prepared via condensation of pyrrole derivative III and indole derivative IV. The prepared indolinone derivative V was found to inhibit DNA-PK (IC50 = 1.6 μM). The experimental process involved the reaction of 6-Chloro-2,3-dihydro-1H-indole(cas: 52537-00-5).Electric Literature of 52537-00-5

The Article related to sulfonamide indolinone preparation inhibitor dna dependent protein kinase, pyrrole carboxaldehyde indolone condensation, Heterocyclic Compounds (One Hetero Atom): Indoles, Indolizines, Carbazoles, and Other Arenopyrroles and other aspects.Electric Literature 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 January 24, 2011, Roca-Lopez, David; Merino, Pedro; Sayago, Francisco J.; Cativiela, Carlos; Herrera, Raquel P. published an article.Electric Literature of 79815-20-6 The title of the article was Organocatalyzed Michael addition reaction by novel (2R,3aS,7aS)-octahydroindole-2-carboxylic acid, a new fused proline. And the article contained the following:

The authors present their results on the organocatalytic enantioselective Michael addition reaction of acetone to different nitroolefines using (2R,3aS,7aS)-octahydroindole-2-carboxylic acid [(R,S,S)-Oic] as a new and suitable catalyst. Computational calculations support the results obtained with (R,S,S)-Oic vs. its diastereomeric form (S,S,S)-Oic. The final products are obtained in good yields and moderate enantioselectivities (up to 58% ee). The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Electric Literature of 79815-20-6

The Article related to acetone nitroolefin michael addition, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Ketones and Derivatives, Including Quinones and Sulfur Analogs and other aspects.Electric Literature 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

Georgieva, Miglena K.; Duarte, Filipe J. S.; Santos, A. Gil published an article in 2016, the title of the article was Directed electrostatic activation in enantioselective organocatalytic cyclopropanation reactions: a computational study.COA of Formula: C9H9NO2 And the article contains the following content:

Cyclopropane rings are versatile building blocks in organic chem. Their synthesis, by the reaction of sulfur ylides with α,β-unsaturated carbonyl compounds, has recently aroused renewed interest after the discovery of efficient catalysis by using (S)-indoline-2-carboxylic acid. In order to rationalize the behavior of this catalyst, MacMillan proposed a directed electrostatic activation (DEA) mechanism, in which the neg. carboxylate group interacts with the pos. thionium moiety, thus reducing the activation energy and increasing the reaction rate. More recently, Mayr refuted some of MacMillan conclusions, but accepted the DEA mechanism as a justification for the exptl. high reaction rates. In contrast, our results indicate that the selectivity obtained in the process seems to result from several strong hydrogen bond interactions between the two reacting species, while no strong evidence for a DEA mechanism was found. We also concluded that the hydrogen bonds don’t improve the reaction rate by lowering the activation energy of the rate-determining step, but can do it by promoting efficient reaction trajectories due to long-range complexation of the reagents. Finally, our results confirm that the cyclopropanation reaction occurs by a two-step mechanism, and that the overall enantioselectivity depends on the relative energies of the two steps, averaged by the relative populations of the iminium intermediates that are initially formed in the reaction. The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).COA of Formula: C9H9NO2

The Article related to enantioselective cyclopropanation catalyst mechanism kinetics activation energy, Physical Organic Chemistry: Theoretical Organic Chemical Concepts, Including Quantum and Molecular Mechanical Studies and other aspects.COA of Formula: C9H9NO2

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 31, 2009, Luo, Ren-Shi; Weng, Jiang; Ai, Hui-Bing; Lu, Gui; Chan, Albert S. C. published an article.Application In Synthesis of H-Idc-OH The title of the article was Highly efficient asymmetric Michael reaction of aldehydes to nitroalkenes with diphenylperhydroindolinol silyl ethers as organocatalysts. And the article contained the following:

New dihydroindole and perhydroindole derivatives were synthesized in good yields and evaluated as chiral catalysts in the asym. Michael reaction of aldehydes to nitroalkenes. (2S,3aS,7aS)-Diphenylperhydroindolinol silyl ether facilitated the reaction of a wide range of aldehyde and nitroalkene substrates, providing Michael adducts in nearly optically pure form (99% ee), good yields and high diastereoselectivities (syn/anti up to 99:1). These results show that perhydroindole derivatives can be highly efficient organocatalysts for the asym. Michael reaction, exhibiting comparable or even better enantioselectivities than proline derivatives The experimental process involved the reaction of H-Idc-OH(cas: 79815-20-6).Application In Synthesis of H-Idc-OH

The Article related to michael stereoselective aldehyde nitroalkene silyloxydiphenylmethylindole catalyst, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Aldehydes and Derivatives, Including Sulfur Analogs and other aspects.Application In Synthesis 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 December 31, 2022, Tan, Jian-Ping; Li, Kehan; Shen, Boming; Zhuang, Cheng; Liu, Zanjiao; Xiao, Kai; Yu, Peiyuan; Yi, Bing; Ren, Xiaoyu; Wang, Tianli published an article.Safety of 1,5-Dimethyl-1H-indole-2-carbaldehyde The title of the article was Asymmetric synthesis of N-bridged [3.3.1] ring systems by phosphonium salt/Lewis acid relay catalysis. And the article contained the following:

Here, a general and modular method for constructing these pseudo-natural N-bridged [3.3.1] ring systems via cascade process by bifunctional phosphonium salt/Lewis acid relay catalysis were reported. A wide variety of substrates bearing an assortment of functional groups (59 examples) were compatible with this protocol. Other features include a [3 + 2] cyclization/ring-opening/Friedel-Crafts cascade pathway, excellent reactivities and stereoselectivities, easily available starting materials, step economy and scalability. The obtained enantioenriched products showed potential of preliminary anticancer activities. Insights gained from our studies are expected to advance general efforts towards the catalytic synthesis of challenging even unprecedented chiral PNPs, offering new opportunities for bioactive small-mol. discovery. 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 bridged indole alkaloid preparation antitumor, Heterocyclic Compounds (One Hetero Atom): Other Areno- and Diarenopyridines (Acridines, Quinolizines, etc.) 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 November 30, 2000, Mavunkel, Babu J.; Chakravarty, Sarvajit; Perumattam, John J.; Dugar, Sundeep; Lu, Qing; Liang, Xi published a patent.Electric Literature of 256935-86-1 The title of the patent was Preparation of 5-[4-benzylpiperidinyl(piperazinyl)]-indolecarboxamides as inhibitors of p38 kinase. And the patent contained the following:

The title compounds [I; one Z2 = CA, CR8A and the other = CR1, CR12, NR6, N (wherein R1, R6, R8 = H, noninterfering substituent; A = WiCOXjY; Y = COR2, an isostere; R2 = H, noninterfering substituent; W, X = spacer of 2-6Å; i, j = 0-1); Z3 = NR7, O; R3 = noninterfering substituent; n = 0-3; L1, L2 = linker; R4 = noninterfering substituent; m = 0-4; Z1 = CR5, N (R5 = H, noninterfering substituent); l, k = 0-2, wherein the sum of l and k = 0-3; Ar = aryl substituted with 0-5 noninterfering substituents, wherein two noninterfering substituents can form a fused ring; the distance between the atom of Ar linked to L2 and the center of the α ring is 4.5-24Å] which inhibit p38-α kinase (biol. data given), were prepared Thus, treating 6-methoxy-(4-benzylpiperidinyl)-indole-5-carboxamide with oxalyl chloride in CH2Cl2 afforded the indole-5-carboxamide II. The experimental process involved the reaction of 6-Chloro-1H-indole-5-carboxylic acid(cas: 256935-86-1).Electric Literature of 256935-86-1

The Article related to indolecarboxamide benzylpiperidinyl benzylpiperazinyl preparation p38 kinase inhibitor, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazines and Quinoxalines (Including Piperazines) and other aspects.Electric Literature of 256935-86-1

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