5059-30-3

Usage

Uses

Used in Pharmaceutical Industry:
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is used as a pharmaceutical intermediate for the development of various drugs. Its unique chemical structure allows it to be a key component in the synthesis of different pharmaceutical compounds.
Used in Synthesis of Indole Phytoalexin Cyclobrassinon:
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is utilized in the synthesis of cyclobrassinon, an indole phytoalexin. Phytoalexins are antimicrobial secondary metabolites produced by plants in response to pathogen attack, and cyclobrassinon is one such compound derived from the Brassicaceae family of plants.
Used in Biomimetic Synthesis of Erucalerin:
2-CHLORO-1H-INDOLE-3-CARBALDEHYDE is also employed in the unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum. 2-CHLORO-1H-INDOLE-3-CARBALDEHYDE contributes to the plant's defense mechanism against pathogens and can be used as a model for developing new bioactive compounds with potential applications in various industries.

InChI:InChI=1/C9H6ClNO/c10-9-7(5-12)6-3-1-2-4-8(6)11-9/h1-5,11H

Upstream product

• 7135-31-1 2-chloro-1H-indole 
• 75-50-3 trimethylamine 
• 68-12-2 N,N-dimethyl-formamide 
• 487-89-8 Indole-3-carboxaldehyde 
• 134792-58-8 1-tosyloxyindole 
• 25250-89-9 2H-indol-2-one 
• 59-48-3 2-oxoindole 
• 127-19-5 N,N-dimethyl acetamide 
• 86531-02-4 1H-indol-1-yl benzoate 
• 134792-59-9 1-(t-butyldimethylsilyloxy)indole 
• 54698-11-2 1-methoxyindole 

Downstream Products

• 38367-57-6 2-Imino-9H-1,3-thiazino[6,5-b]indole 
• 68640-95-9 1-acetyl-2-chloro-1H-indole-3-carbaldehyde 
• 90815-04-6 2-Chloro-1-(3,4-dichloro-benzyl)-1H-indole-3-carbaldehyde 
• 90815-05-7 2-Chloro-1-(2,4-dichloro-benzyl)-1H-indole-3-carbaldehyde 
• 75621-51-1 1-(4-Chlorobenzyl)-2-chloroindole-3-carboxaldehyde 
• 75621-49-7 1-(2-Chlorobenzyl)-2-chloroindole-3-carboxaldehyde 
• 145235-87-6 2-chloro-N-(methoxymethyl)indole-3-carbaldehyde 
• 121138-67-8 2-chloro-1-(pent-4-enyl)-1H-indole-3-carboxaldehyde 
• 77655-47-1 1-(p-metossibenzil)-2-cloroindol-3-carbossialdeide 
• 24279-74-1 2-chloro-1-methyl-1H-indole-3-carboxaldehyde 
• 75621-56-6 2-Chloro-1-(3-methoxy-benzyl)-1H-indole-3-carbaldehyde 
• 93548-83-5 2-Chloro-1-(3,5-dichloro-benzyl)-1H-indole-3-carbaldehyde 
• 93548-79-9 2-Chloro-1-(2,5-dichloro-benzyl)-1H-indole-3-carbaldehyde 
• 75621-50-0 1-(3-Chlorobenzyl)-2-chloroindole-3-carboxaldehyde 

Relevant academic research and scientific papers

Synthesis and Antibacterial Activity of Novel 1H-indol-2-ol Derivatives

A series of novel 1H-indol-2-ol derivatives were synthesized and evaluated their antibacterial activities against rice bacterial leaf blight, tobacco bacterial wilt, and citrus canker caused by Xanthomonas oryzae pv. oryzae (Xoo), Ralstonia solanacearum, and Xanthomonas axonopodis pv. citri via the turbidimeter test in vitro. Antibacterial bioassay indicated that most compounds demonstrated good inhibitory effect against Xoo and Ralstonia solanacearum. Especially, compound 4k demonstrated the best inhibitory effect against Xoo with half-maximal effective concentration (EC50) value of 8.27?μg/mL, which was even better than those of commercial agents Bismerthiazol and Thiodiazole copper.

Stereoselective synthesis of novel annulated thiopyrano indole derivatives from simple oxindole via intramolecular 1,3-dipolar cycloaddition reactions of nitrone and nitrile oxide

Synthesis of some novel isoxazolidine/dihydroisoxazole annulated thiopyrano[2,3-b]indole derivatives from simple oxindole via 1,3-dipolar cycloaddition reaction involving nitrone and nitrile oxide as 1,3-dipole is reported.

Recyclable and reusablen-Bu4NBF4/PEG-400/H2O system for electrochemical C-3 formylation of indoles with Me3N as a carbonyl source

A safe, practical and eco-friendly electrochemical methodology for the synthesis of 3-formylated indoles has been developed by the utilization of Me3N as a novel formylating reagent. Stoichiometric oxidants, metal catalysts, and activating agents were avoided in this method, and an aqueous biphasic system ofn-Bu4NBF4/PEG-400/H2O was used as a recyclable and reusable reaction medium, which made this electrosynthesis approach more sustainable and environmentally friendly. This process expanded the substrate scope and functional group tolerance for bothN-EDG andN-EWG indoles. Furthermore, late-stage functionalization and total/formal synthesis of drugs and natural products were realized by means of this route.

A cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes to access thieno[2,3-b]indoles and benzothiophenes

The first catalyst-free cascade deprotonation/intramolecular aldol reaction of α-carbonyl sulfonium ylides with 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes was developed. A series of thieno[2,3-b]indoles and benzothiophenes were smoothly obtained in high to excellent yields. The salient features of the protocol include catalyst-free conditions, an environment-friendly solvent, broad substrate scope, and large-scale synthesis.

ORGANIC ELECTROLUMINESCENT COMPOUND AND ORGANIC ELECTROLUMINESCENT DEVICE COMPRISING THE SAME

The present application relates to an organic electroluminescent compound represented by chemical formula 1, and an organic electroluminescent device comprising the same. By comprising the organic electroluminescent compound of the present application having good thermal stability, it is possible to provide the organic electroluminescent device having lower driving voltage, high luminous efficiency and/or long lifespan characteristics compared with an existing organic electroluminescent device.COPYRIGHT KIPO 2020

INDOLE-YNONE MEDIATED BENZOANNULATION PROCESS FOR THE PREPARATION OF CARBAZOLES- CARBAZOMYCIN A, CALOTHRIXIN B AND STAUROSPORINONE

The present invention relates to carbazoles of general formula (I), and process for the preparation thereof: wherein 'R1' is H, C1-C6 alkyl, benzyl, or allyl; R2 is H, C1-C6 alkyl, cyclopropyl, phenyl, aryl, heteroaryl, or NO2; R3 is H, C1-C6 alkyl, cyclopropyl, phenyl aryl, heteroaryl, 4-methoxy phenyl, 4-ethyl phenyl, 2-methyl phenyl, or 2-Fluoro phenyl; R4 is H, benzoyl, -CO2Et, -CHO, Br, or -OMe; R5 is OH, OMOM, OMe, CN, or OTf; R6 is H, or O-alkyl; and R3-R4 is -CHNCH2CH2-. This invention also relates to the process for the preparation of carbazomycin A of Formula (1), calothrixin B of Formula (2) and staurosporinone of Formula (3) involving carbazoles of general formula (I) as an intermediate.

Organocatalytic enantioselective tandem sulfa-Michael/aldol reaction to access dihydrothiopyran-fused benzosulfolane skeletons bearing three contiguous stereocenters

The first organocatalytic diastereo- and enantioselective tandem sulfa-Michael/aldol reaction of 2-mercaptoindole-3-carbaldehydes and 2-mercaptobenzaldehydes with benzo[b]thiophene sulfones was developed. With multiple hydrogen-bonding thiourea as a catalyst, a wide range of polycyclic dihydrothiopyran-fused benzosulfolanes were smoothly obtained with excellent results (up to 99% yield, 420 : 1 dr and 99% ee) under mild reaction conditions.

Synthesis, Antiviral Activity, and Induction of Plant Resistance of Indole Analogues Bearing Dithioacetal Moiety

A series of compounds with potential activity to induce plant resistance was synthesized from indole and thiol compounds and methodically evaluated for antiviral activity. The results indicated that some of the synthesized compounds had high antipotato virus Y (PVY), anticucumber mosaic virus, and antitobacco mosaic virus activities. Notably, compound D21 exhibited the best activity against PVY among these compounds in vivo, and the 50% effective concentrations (EC50) of protection activity is 122 μg/mL, which was distinctively better than the corresponding values for ribavirin (653 μg/mL), Ningnanmycin (464 μg/mL), and Xiangcaoliusuobingmi (279 μg/mL). Interestingly, we found that the protection activity of D21 was associated with improvement of chlorophyll content and defense-related enzyme activities. Moreover, D21 could trigger the malate dehydrogenase (MDH) signaling pathway, as further confirmed by the MDH activity evaluation. Hence, D21 can protect plants against viral activity and has potential as a novel activator for plant resistance induction.

Benzpyrole derivative containing dithioacetal unit, preparation method and application thereof

The invention discloses a benzpyrole derivative containing a dithioacetal unit, a preparation method and application thereof. The benzpyrole derivative has the general structural formula (I) (being defined as in the specification), in the formula, R1 is substitution hydrogen or a halogen atom, R2 is a substitution aromatic ring, 1-propyl alcohol, methyl, ethyl, propyl, isopropyl, butyl, isobutyl or dodecyl, and X is a halogen atom and the methyl. The benzpyrole derivative has the good biological activity for plant virus diseases, the preparation process is simple, and the production cost is low.

Monodentate Transient Directing Group Enabled Pd-Catalyzed Ortho-C-H Methoxylation and Chlorination of Benzaldehydes

We report Pd-catalyzed ortho-C-H methoxylation and chlorination of benzaldehydes by employing monodentate transient directing groups (TDGs) as an alternative strategy to bidentate TDGs. More importantly, a single crystal of benzaldehyde imine ortho-cyclopalladium intermediate was successfully obtained, and its structure was unambiguously determined by X-ray diffraction, which clearly showed that it was a binuclear palladium species bridged by a pyridone ligand. The utility of this approach was further demonstrated through the synthesis of key intermediates of natural products and drugs.