61675-16-9

Upstream product

• 15903-94-3 6-benzyloxy-1H-indole 
• 74-88-4 methyl iodide 
• 75-93-4 methyl bisulfate 
• 32503-27-8 tetra(n-butyl)ammonium hydrogensulfate 

Downstream Products

• 202807-53-2 (6-benzyloxy-1-methyl-1H-indol-3-yl)-oxo-acetyl chloride 
• 941575-97-9 C₂₀H₁₉NO₄ 
• 941575-85-5 3-(benzofuran-3-yl)-4-(6-benzyloxy-1-methyl-1H-indol-3-yl)pyrrole-2,5-dione 
• 941575-86-6 3-(6-benzyloxy-1-methyl-1H-indol-3-yl)-4-(5-fluorobenzofuran-3-yl)pyrrole-2,5-dione 
• 1158209-47-2 6-benzyloxy-1-methyl-1H-indole-3-sulfonyl chloride 
• 1600500-92-2 6-benzyloxy-1-methyl-1H-indole-3-carbonitrile 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Regioselective C?H Allylation and Prenylation of Indoles at C4-Position

Herein, Rh(III)-catalyzed C4-selective C?H allylation and prenylation of indoles by using a weak carbonyl coordination directing group have been reported. By employing 5-methylene-1,3-dioxan-2-ones, 4-vinyl-1,3-dioxolan-2-ones and 2-methyl-2,3-butadiene as scalable cross-coupling partners, these divergent synthesis protocols proceed smoothly under redox-neutral reaction conditions, delivering various allylated and prenylated indoles in moderate to satisfied yields. This transformation exhibits high functional-groups compatibility and broad substrate scope. Scale-up experiment and mechanistic studies were also accomplished. (Figure presented.).

Metal-Free Oxidative Cross Coupling of Indoles with Electron-Rich (Hetero)arenes

A new method for the synthesis of bi-heteroaryls is reported, based on the umpolung of indoles with benziodoxol(on)e hypervalent iodine reagents (IndoleBX). The oxidative coupling of IndoleBX with an equimolar amount of electron-rich benzenes, indoles, pyrroles, and thiophenes proceeded under mild transition-metal-free conditions. Functionalized non-symmetrical bi-indolyl heterocycles were accessed efficiently. Introduction of a new type of C2-substituted indole benziodoxole reagents further allowed extending the scope of the reaction to NH unprotected and C3-alkylated indoles. The obtained bi-heterocycles are important building blocks in synthetic and medicinal chemistry, and could be easily transformed into more complex heterocyclic systems.

Access to Air-Stable 1,3-Diphosphacyclobutane-2,4-diyls by an Arylation Reaction with Arynes

Tuning of the physicochemical properties of the 1,3-diphosphacyclobutane-2,4-diyl unit is attractive in view of materials applications. The use of arynes is shown to be effective for installing relatively electron rich aryl substituents into the open-shell singlet P-heterocyclic system. Treatment of the sterically encumbered 1,3-diphosphacyclobuten-4-yl anion with ortho-silylated aryl triflates in the presence of fluoride under appropriate conditions afforded the corresponding 1-aryl 1,3-diphosphacyclobutane-2,4-diyls. The air-stable open-shell singlet P-heterocycles exhibit considerable electron-donating character, and the aromatic substituent influences the open-shell character, which is thought to be related to the property of p-type semiconductivity. The P-arylated 1,3-diphosphacyclobutane-2,4-diyl systems can be further utilized as detectors of hydrogen fluoride (HF), which causes a remarkable change in their photoabsorption properties.

Zinc-catalyzed direct cyanation of indoles and pyrroles: Nitromethane as a source of a cyano group

With nitromethane and diphenylsilane (Ph2SiH2), zinc triflate behaves as a Lewis acid catalyst for the cyanation of nitrogen-containing heteroarenes such as indoles and pyrroles. This is the first realization of the Lewis acid-catalyzed direct cyanation of a C(aryl)-H bond with no CN group-containing cyanating agent.

Structure-based design leads to the identification of lithium mimetics that block mania-like effects in rodents. Possible new GSK-3β therapies for bipolar disorders

More than two million American adults, or approximately one percent of the population 18 years or older, suffer from bipolar disorder. Current treatments include the so-called "mood stabilizers," lithium and valproic acid. Both are relatively dated drugs that are only partially effective and produce various undesirable side effects including weight gain. Based upon continued efforts to understand the molecular target for lithium, it now appears that specific inhibitors of the enzyme glycogen synthase kinase-3β (GSK-3β) may mimic the therapeutic action of mood stabilizers and might therefore allow for the design of improved drugs for treating patients with bipolar disorder as well as certain neurodegenerative disorders. Furthermore, the pro-apoptotic properties of the GSK-3 enzyme suggest the possible use of such inhibitors as neuroprotective agents. In fact, neuroprotection may contribute to the treatment of mood disorders. The present chemistry, modeling, and biology efforts have identified 3-benzofuranyl-4-indolylmaleimides as potent and relatively selective GSK-3β inhibitors. The best ligand in this series (having a Ki value of 4.6 nM against GSK-3β) was studied in a novel mouse model of mania that has recently been validated with several clinically effective mood stabilizers. This study presents the first demonstration of the efficacy of a GSK-3β inhibitor in this mouse model of mania. Selective brain penetrable GSK-3 ligands like those described herein become valuable research tools in better defining the role of this multifaceted kinase in both physiological and pathophysiological events.

Tinctorial compositions for keratin fibres containing precursors of oxidation colorants and indole couplers, and dyeing processes using these compositions

Tinctorial composition for keratin fibers, containing a para-type precursor of an oxidation colorant associated with a heterocyclic coupler of formula: STR1 where R1 =H, or C1 -C4 alkyl; R2 and R3, wh

Process for dyeing keratin fibres with a monohydroxyindole associated with an iodide and hydrogen peroxide

Process for dyeing keratin fibres consisting in applying on these fibres a composition (A) containing at least one indole colorant of formula: STR1 where R1 =H or C1 -C4 alkyl; R2 and R3, which may be identical or different, denote H, C1 -C4 alkyl, carboxyl or alkoxycarbonyl; or a salt or a precursor of a compound (I), associated, either with iodide ions, or with H2 O2 ; application of composition (A) being preceded or followed by the application of a compound (B) which contains, either H2 O2 at a pH of 2 to 12 when (A) contains iodide ions, or iodide ions at a pH of 2 to 11 when (A) contains H2 O2. This process allows particularly powerful and resistant dyes to be made.