20538-21-0

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 55, p. 3688, 1990 DOI: 10.1021/jo00298a064

InChI:InChI=1/C21H17NO/c23-21(17-10-3-1-4-11-17,18-12-5-2-6-13-18)20-15-16-9-7-8-14-19(16)22-20/h1-15,22-23H

Upstream product

• 126594-12-5 <1-<(N,N-dimethylamino)methyl>indol-2-yl>diphenylmethanol 
• 119-61-9 benzophenone 
• 139409-34-0 2-bromo-1H-indole 
• 86531-02-4 1H-indol-1-yl benzoate 
• 3289-82-5 1-hydroxyindole 
• 134792-59-9 1-(t-butyldimethylsilyloxy)indole 
• 5379-79-3 N-(dimethylaminomethyl)indole 
• 120-72-9 indole 
• 54698-11-2 1-methoxyindole 
• 144219-54-5 1-methoxymethoxyindole 
• 496-15-1 1-indoline 
• 144219-59-0 α,α-diphenyl-1-(methoxymethoxy)indole-2-methanol 
• 134792-66-8 (1-Methoxy-1H-indol-2-yl)-diphenyl-methanol 
• 3770-50-1 2-carbethoxyindole 

Relevant academic research and scientific papers

Synergistic catalysis for asymmetric [3 + 2] cycloadditions of 2-indolylmethanols with α,β-unsaturated aldehydes

A catalytic asymmetric [3 + 2] cycloaddition of 2-indolylmethanols with α,β-unsaturated aldehydes was developed for the first time. This transformation was achieved by a synergistic catalytic system consisting of a palladium complex, a Br?nsted acid, and a chiral secondary amine to synthesize biologically active cyclopenta[b]indole derivatives with excellent diastereo- A nd enantioselectivities (up to >20:1 dr, up to 99% ee).

Temperature-controlled regioselective thiolation of 2-indolylmethanols under aqueous micellar conditions

A sustainable and regioselective synthesis of highly functionalized indole-based sulfides from thiols and 2-indolymethanols is described. Notably, this reaction can be performed in the presence of 5 mol% In(OTf)3 under aqueous micellar conditions using an inexpensive surfactant DBSA. This protocol offers several advantages including excellent regioselectivities, being organic solvent-free, ease of scale-up, broad substrate scope, and recycling of the aqueous reaction medium and catalyst.

Atroposelective Synthesis of 3,3’-Bisindoles Bearing Axial and Central Chirality: Using Isatin-Derived Imines as Electrophiles

An atroposelective synthesis of a new class of 3,3’-bisindoles bearing axial and central chirality has been established via catalytic asymmetric addition reactions using isatin-derived imines as electrophiles (23 examples, up to 80% yield, > 95 : 5 dr, 98 : 2 er). This approach takes advantage of chiral phosphoric acid-catalyzed dynamic kinetic resolution of 2-substituted 3,3’-bisindoles via nucleophilic addition of such substrates with isatin-derived imines. In this approach, isatin-derived imines acted as a class of competent electrophiles due to their high reactivity and bulky size, which provided an easy access to axially chiral 3,3'-bisindoles incorporated with a biologically important chiral 3-aminooxindole unit. This approach has greatly expanded the generality and applicability of the strategy of dynamic kinetic resolution for the synthesis of enantioenriched 3,3’-bisindole derivatives bearing both axial and central chirality.

Cooperation of Mn(III)/Br?nsted acid for the synthesis of quindoline derivatives via dehydroxylation/azidation/cyclization cascade of diaryl(1 H-indol-2-yl)methanols with trimethylsilyl azide

A new synthesis of quindoline derivatives promoted by Mn(III)/Br?nsted acid via a dehydroxylation/azidation/cyclization cascade of diaryl(1H-indol-2-yl)methanols with trimethylsilyl azide was developed. The reaction features very effective transformation involving two C(sp2)-H and one C(sp3)-O bond cleavages, two C(sp2)-N bonds, and one N-heterocycle formation in a one-pot manner. A series of 11-arylquindolines were synthesized in good yields.

Nitrogen heterocyclic ring-containing organic electroluminescent compound as well as preparation method and application thereof

The invention provides a nitrogen heterocyclic ring-containing organic electroluminescent compound, as well as a preparation method and application thereof. The nitrogen heterocyclic ring-containing organic electroluminescent compound has a structure as s

Regio- and Enantioselective (3+3) Cycloaddition of Nitrones with 2-Indolylmethanols Enabled by Cooperative Organocatalysis

The regio- and enantioselective (3+3) cycloaddition of nitrones with 2-indolylmethanols was accomplished by the cooperative catalysis of hexafluoroisopropanol (HFIP) and chiral phosphoric acid (CPA). Using this approach, a series of indole-fused six-membered heterocycles were synthesized in high yields (up to 98 %), with excellent enantioselectivities (up to 96 % ee) and exclusive regiospecificity. This approach enabled not only the first organocatalytic asymmetric (3+3) cycloaddition of nitrones but also the first C3-nucleophilic asymmetric (3+3) cycloaddition of 2-indolylmethanols. More importantly, theoretical calculations elucidated the role of the cocatalyst HFIP in helping CPA control the reactivity and enantioselectivity of the reaction, demonstrating a new mode of cooperative catalysis.

Synthesis of indole-fused scaffolds via [3+3] cyclization reaction of 2-indolylmethanols with quinone imines

A formal [3 + 3] cyclization reaction of 2-indolylmethanols with quinones was realized to furnish indole-fused scaffolds in moderate to excellent yields. This protocol was proceeded smoothly under acid condition, with high high yields and broad substrate scope.

Lithiation of 1-alkoxyindole derivatives

Lithiation of 1-alkoxyindoles, 3-dimethylaminomethyl- and 3-dimethylaminoethyl-1-methoxyindole occurred regioselectively at the 2-position. The introduction of a sterically bulky group into the 2-position of 3-dimethylaminomethyl-1-methoxyindoles directed the lithiation to the 4-position.

Substrate-Controlled Regioselective Arylations of 2-Indolylmethanols with Indoles: Synthesis of Bis(indolyl)methane and 3,3′-Bisindole Derivatives

A substrate-controlled regioselective arylation of 2-indolylmethanols with indoles has been established, which efficiently afforded bis(indolyl)methane and 3,3′-bisindole derivatives in high yields and with a broad substrate scope (up to 98% yield, 36 examples). This approach will not only provide an important strategy for the diversified synthesis of bis(indolyl)methane and 3,3′-bisindole derivatives but also serve as a good example for substrate-controlled regioselective reactions.

A REGIOSELECTIVE LITHIATION OF 1-METHOXYMETHOXYINDOLE AT THE 2-POSITION AND ITS APPLICATION FOR THE SYNTHESIS OF 2-SUBSTITUTED INDOLES

A regioselective lithiation of 1-methoxymethoxyindole at the 2-position was achieved with n-BuLi at 0 deg C.Subsequent treatment with electrophiles afforded 2-substituted 1-methoxymethoxyindoles, which were readily converted to 2-substituted indoles.