67282-55-7

Upstream product

• 186581-53-3 diazomethane 
• 67282-51-3 1-hydroxy-1H-indole-3-carbaldehyde 
• 54698-11-2 1-methoxyindole 
• 127-19-5 N,N-dimethyl acetamide 
• 68-12-2 N,N-dimethyl-formamide 
• 496-15-1 1-indoline 
• 3289-82-5 1-hydroxyindole 
• 69111-94-0 3-(dimethylaminomethyl)-1-methoxyindole 
• 20973-67-5 N,N-dimethyl-2-(2-nitrophenyl)ethenylamine 
• 88-72-2 1-methyl-2-nitrobenzene 
• 86531-02-4 1H-indol-1-yl benzoate 
• 32991-03-0 trans-β-dimethylamino-2-nitrostyrene 
• 386715-37-3 2-(2-nitrophenyl)malondialdehyde 
• 724706-20-1 4-ethyl 1-methyl 2-cyano-2-(2-nitrophenyl)succinate 

Downstream Products

• 113866-44-7 brassicanal A 
• 110139-35-0 N-methoxyindole-3-methanol 
• 22259-53-6 3-aminomethylindole 
• 68156-97-8 (+/-)-6,7-seco-agroclavine 
• 487-89-8 Indole-3-carboxaldehyde 
• 67282-51-3 1-hydroxy-1H-indole-3-carbaldehyde 
• 5541-89-9 4-(1H-indol-3-yl)-2-butanone 

Relevant academic research and scientific papers

A new general synthesis of N-hydroxyindoles

Catalytic hydrogenation of 2-nitrobenzyl aldehydes, ketones and amides, using Pd/C and (Ph3P)4Pd, affords N-hydroxyindoles in good to excellent overall yields. Georg Thieme Verlag Stuttgart.

Mechanochemical Synthesis and Isomerization of N-Substituted Indole-3-carboxaldehyde Oximes ?

Performing solution-phase oximation reactions with hydroxylamine hydrochloride (NH2OH·HCl) carries significant risk, especially in aqueous solutions. In the present study, four N-substituted indole-3-carboxaldehyde oximes were prepared from the corresponding aldehydes by solvent-free reaction with NH2OH·HCl and a base (NaOH or Na2CO3) using a mechanochemical approach, thus minimizing the possible risk. In all cases, the conversion to oximes was almost complete. The focus of this work is on 1-methoxyindole-3-carboxaldehyde oxime, a key intermediate in the production of indole phytoalexins with useful antimicrobial properties. Under optimized conditions, it was possible to reach almost 95% yield after 20 min of milling. Moreover, for the products containing electron-donating substituents (-CH3, -OCH3), the isomerization from the oxime anti to syn isomer under acidic conditions was discovered. For the 1-methoxy analog, the acidic isomerization of pure isomers in solution resulted in the formation of anti isomer, whereas the prevalence of syn isomer was observed in solid state. From NMR data the syn and anti structures of produced oximes were elucidated. This work shows an interesting and possibly scalable alternative to classical synthesis and underlines environmentally friendly and sustainable character of mechanochemistry.

Novel 1-methoxyindole- and 2-alkoxyindole-based chalcones: design, synthesis, characterization, antiproliferative activity and DNA, BSA binding interactions

Indole-based chalcones have been identified as interesting compounds with anticancer properties. In the present study, we report the synthesis and evaluation of new 1-methoxyindole and 2-alkoxyindole chalcone hybrids as antiproliferative agents active aga

Cu-mediated oxidative dimerization of skatole to tryptanthrin, an indolo[2,1-b]quinazolone alkaloid

A one-pot conversion of skatole to tryptanthrin, an indolo[2,1-b]quinazoline alkaloid, was achieved by Cu-mediated oxidation.

Synthesis and anti-inflammatory activity of indole glucosinolates

The nitronate and nitrovinyl methods to synthesize indole glucosinolates (GLs) have been investigated. The results were applied to generally the most prevalent natural indole glucosinolates to synthesize 4-methoxyglucobrassicin (MGB) and neo-glucobrassici

Efficient total syntheses of phytoalexin and (±)-paniculidine B and C based on the novel methodology for the preparation of 1-methoxyindoles

A general route to 2-unsubstituted-1-methoxyindoles, based on our methodology for the synthesis of 1-methoxyindoles, is reported. This synthesis renders accessibility to a variety of natural products possessing the said skeleton. A direct synthesis of phy

A General Synthesis of N-Hydroxyindoles

A general method for the formation of N-hydroxyindoles is demonstrated through a lead-promoted intramolecular reductive cyclization of o-nitrobenzyl ketones and aldehydes under transfer hydrogenation conditions. The N-hydroxyindoles are isolated in high purity and excellent yield (> 90%) in an operationally simple procedure. This new method is exemplified by a two-step synthesis of the naturally occurring 1-methoxyindole-3-carboxaldehyde, which is pivotal in many alkaloid total syntheses.

Syntheses of wasabi phytoalexin (methyl 1-methoxyindole-3-carboxylate) and its 5-iodo derivative, and their nucleophilic substitution reactions

A simple synthetic method for methyl 1-methoxyindole-3-carboxylate, a phytoalexin isolated from Wasabia japonica, syn. Eutrema wasabi, and its 5-iodo derivative is reported. They underwent nucleophilic substitution reactions selectively at the 2-position.

PREPARATION OF 1-HYDROXYINDOLE DERIVATIVES AND A NEW ROUTE TO 2-SUBSTITUTED INDOLES

An easy handling method of 1-hydroxyindole is developed.Based on the method, preparation and reaction of 1-hydroxyindole derivatives are investigated.A new regioselective lithiation of 1-methoxyindole and its application for the synthesis of 2-substituted indoles are also reported.

Structure function relationship study of yuehchukene. I. Anti-implantation and estrogenic activities of substituted yuehchukene derivatives

(+/-)-Yuehchukene (YCK) is a novel bis-indole alkaloid with potent anti-implantation activity in rats.The present paper reports the activity of YCK derivatives by substitution on the parent compound.Substitutions on the indole nitrogens or on 2- and 5'-positions of the indole moiety abolished activity.N-1'-methylation of the free indole only permitted a 30percent residual activity.Saturation of the C9-C10 cyclohexenyl double bond did not affect activity at all.Hydroxylation, whether on the C9-C10 double bond, or at C2 or C5, rendered the hydroxylated derivatives inactive.This suggests that the active metabolite in anti-implantation was probably not a hydroxylated derivative carrying estrogenic activity.