102016-76-2

Upstream product

• 608-07-1 2-(5-methoxyindol-3-yl)ethylamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 66-83-1 5-methoxytryptamine hydrochloride 
• 250672-50-5 1-(tert-butyldimethylsilyl)-3-bromo-5-methoxy-1H-indole 
• 162710-95-4 1-(tert-Butyldimethylsilyl)-5-methoxyindole 
• 1006-94-6 5-methoxylindole 
• 335451-49-5 1-(tert-Butyldimethylsilyl)-5-methoxy-N-(4-methylbenzenesulfonyl)tryptamine 

Downstream Products

• 2009-03-2 5-methoxy-N-methyltryptamine 
• 1318072-93-3 C₂₈H₃₈N₂O₄SSi 
• 1334298-37-1 N-(2-(5-methoxy-1-methyl-1H-indol-3-yl)ethyl)-4-methylbenzenesulfonamide 
• 73-31-4 5-methoxy-N-acetyl-tryptamine 

Relevant academic research and scientific papers

The Plasmodium falciparum eIK1 kinase (PfeIK1) is central for melatonin synchronization in the human malaria parasite. Melatotosil blocks melatonin action on parasite cell cycle

Melatonin and its indoles derivatives are central in the synchronization of malaria parasites. In this research, we discovered that melatonin is unable to increase the parasitemia in the human malaria Plasmodium falciparum that lacks the kinase PfeIK1. Th

Exploration of a KI-catalyzed oxidation system for direct construction of bispyrrolidino[2,3-: B] indolines and the total synthesis of (+)-WIN 64821

A facile and environmentally benign KI(cat.)/NaBO3·4H2O oxidation system has been developed for the tandem oxidative aminocyclization/coupling of tryptamines, affording a series of 3a,3a′-bispyrrolidino[2,3-b]indolines with high efficiency (up to 94% yield). This reaction features an electrophilic "I+" mechanism, which is importantly quite different from and milder than the typical radical-involving process, and can be readily amplified for the total synthesis of (+)-WIN 64821.

Synthesis of Carbolines via Palladium/Carboxylic Acid Joint Catalysis

The combination of a Pd(0) complex with benzoic acid converts propargylic tryptamines to the corresponding tetrahydro-β-carbolines. The method uses unprotected indoles and affords the desired products with ample functional group tolerance. Detailed modeling studies reveal a close synergy between the organic and metal catalysts, which enables sequential alkyne isomerization, indole C-H activation, and eventual C-C reductive elimination to afford the target heterocycles.

Gold-Catalyzed Intramolecular Tandem Cyclization of Indole-Ynamides: Diastereoselective Synthesis of Spirocyclic Pyrrolidinoindolines

A gold-catalyzed intramolecular tandem cyclization of indole-ynamide affords tetracyclic spirocyclic pyrrolidinoindoline bearing an all-carbon quaternary stereocentre in a single step; however, when the reaction was carried out in the presence of BF3·Et2O, the corresponding tricyclic spirocyclic pyrrolidinoindoline-based enones are produced through a key 1,5-hydride shift. The developed chemistry provides a diastereoselective and straightforward entry to structurally diverse polycylic pyrrolidinoindolines from indole-ynamides in one-pot reactions under mild conditions.

CuCl2/TBHP-mediated direct chlorooxidation of indoles

CuCl2/TBHP-mediated direct chlorooxidation of indole derivatives under simple aerobic conditions was reported, leading to facile preparations of a range of 3,3-disubstituted 3-chlorooxindoles in good yields and selectivities.

Ir-catalyzed reverse prenylation of 3-substituted indoles: Total synthesis of (+)-aszonalenin and (-)-brevicompanine B

The selective reverse prenylation of 3-substituted-1H-indoles at C3 is described. The iridium-catalyzed reaction proceeds with high branched to linear selectivity (>20:1) for a variety of indoles. In addition, a diastereoselective reverse prenylation of tryptophan methyl ester is disclosed, and its synthetic utility is demonstrated in the synthesis of (+)-aszonalenin and (-)-brevicompanine B.

Rhodium(I)-catalyzed cycloisomerization of nitrogen-tethered indoles and alkylidenecyclopropanes: Convenient access to polycyclic indole derivatives

At the end of its tether: A new synthetic protocol for the preparation of polycyclic indole derivatives has been developed from a rhodium(I)-catalyzed cycloisomerization of a nitrogen-tethered indole and alkylidenecyclopropane, affording the corresponding

Preparation and reactions of 4-, 5-, and 6-methoxy substituted 3-lithioindoles and 3-indolylzinc derivatives

The preparation of 4-, 5-, and 6-methoxy substituted 3-lithio-1-(trialkylsilyl)indoles 4b-d by metalation of the corresponding 3-bromoindoles, and their reactions with iodomethane, DMF, ethylene oxide and aziridines are reported. Transmetalation of 3-lithioindoles 4b-d with ZnCl2 afforded 3-indolylzinc chlorides 11b-d, which underwent Pd(0)-catalyzed cross-coupling reactions with 2-halopyridines to give 4-, 5-, and 6-methoxy substituted 3-(2-pyridyl)indoles.