137449-25-3

Upstream product

• 673-32-5 1-Phenylprop-1-yne 
• 612-64-6 N-ethyl-N-nitrosoaniline 
• 103-69-5 N-ethyl-N-phenylamine 
• 826-42-6 N,N-diethylaniline N-oxide 
• 14321-27-8 N-ethylbenzylamine 
• 446-52-6 2-Fluorobenzaldehyde 
• 1037132-05-0 2-(benzyl(ethyl)amino)benzaldehyde 
• 67-68-5 dimethyl sulfoxide 
• 78388-92-8 1-(3-methyl-2-phenyl-1H-indol-1-yl)ethan-1-one 
• 644-21-3 1-ethyl-1-phenylhydrazine 

Relevant academic research and scientific papers

Potassium tert-Butoxide-Mediated Condensation Cascade Reaction: Transition Metal-Free Synthesis of Multisubstituted Aryl Indoles and Benzofurans

An efficient and facile method to synthesize valuable disubstituted 2-aryl indoles and benzofurans in good yields has been demonstrated, based on a tert-butoxide-mediated condensation reaction involving a vinyl sulfoxide intermediate. Products are obtained from N- or O-benzyl benzaldehydes using dimethyl sulfoxide as a carbon source. The methodology features a wide functional group tolerance and transition metal-free environment. Preliminary mechanistic studies suggest that the reaction involves a tandem aldol reaction/Michael addition/dehydrosulfenylation/isomerization sequence through an ionic protocol.

Rhodium-catalyzed annulation of tertiary aniline N-oxides to N-alkylindoles: Regioselective C-H activation, oxygen-atom transfer, and N-dealkylative cyclization

[Cp?RhIII]-catalyzed annulation of tertiary aniline N-oxides with alkynes was reported to achieve the challenging ortho C-H functionalization of tertiary anilines via N-O bond acting as a traceless directing group. More significantly, this system represents the first example which integrates C-H activation, oxygen-atom transfer, and N-dealkylative cyclization in one reaction. This unprecedented coupling reaction has allowed the construction of N-alkylindole derivatives in high efficiency with broad substrate scope and good functional group tolerance.

A method for synthesis of indole compounds

The invention provides a method for synthesizing an indole compound. The method comprises the following steps of adding alkali into 2-acyl-N,N-disubstituted phenylamine which serves as a raw material under the protection of nitrogen, and heating the mixture in a solvent to obtain the high-yield indole compound. The raw material is readily available, and the method is convenient to operate, short in reaction time and high in reaction yield, and has high practical value for the industrial preparation of the indole compound.

A Versatile, Traceless C-H Activation-Based Approach for the Synthesis of Heterocycles

A versatile, traceless C-H activation-based approach for the synthesis of diversified heterocycles is reported. Rh(III)-catalyzed, N-amino-directed C-H alkenylation generates either olefination products or indoles (in situ annulation) in an atom- and step-economic manner at room temperature. The remarkable reactivity endowed by this directing group enables scale-up of the reaction to a 10 g scale at a very low catalyst loading (0.01 mol %/0.1 mol %). Ex situ annulation of olefination product provides entry into an array of heterocycles.

Ruthenium(II)-Catalyzed Traceless C?H Functionalization Using an N?N Bond as an Internal Oxidant

A previously elusive RuII-catalyzed N?N bond-based traceless C?H functionalization strategy is reported. An N-amino (i.e., hydrazine) group is used for the directed C?H functionalization with either an alkyne or an alkene, affording an indole derivative or olefination product. The synthesis features a broad substrate scope, superior atom and step economy, as well as mild reaction conditions.

Br?nsted acid cocatalysis in photocatalytic intramolecular coupling of tertiary amines: Efficient synthesis of 2-arylindols

We report herein a highly efficient intramolecular coupling reaction of tertiary amines and ketones (α,β-unsaturated ketones) by using a Br?nsted acid as a cocatalyst, affording 2-arylindols in good to excellent yields (up to 92%) under visible light irra

Intramolecular dehydrative coupling of tertiary amines and ketones promoted by KO-t-Bu/DMF: A new synthesis of indole derivatives

A new synthesis of indole derivatives has been achieved through intramolecular dehydrative coupling of tertiary amines and ketones promoted by KO-t-Bu/DMF. The reaction probably proceeds via an α-amino alkyl radical pathway.

Rhodium(III)-catalyzed indole synthesis using N-N bond as an internal oxidant

We report herein a Rh(III)-catalyzed cyclization of N-nitrosoanilines with alkynes for streamlined synthesis of indoles. The synthetic protocol features a distinct internal oxidant, N-N bond, as a reactive handle for catalyst turnover, as well as a hitherto tantalizingly elusive intermolecular redox-neutral manifold, predicated upon C-H activation, for the formation of a five-membered azaheterocycle. The compatibility of seemingly dichotomous acidic and basic conditions ensures reaction versatility for multifarious synthetic contexts. The tolerance of an array of auxiliary functional groups potentially permits predefined, programmable substitution patterns to be incorporated into the indole scaffold. Comprehensive mechanistic studies, under acidic condition, support [RhCp*]2+ as generally the catalyst resting state (switchable to [RhCp*(OOCtBu)]+ under certain circumstance) and C-H activation as the turnover-limiting step. Given the variety of covalent linkages available for the nitroso group, this labile functionality is likely to be harnessed as a generic handle for strikingly diverse coupling reactions.

Diborane as reducing agent: Part VII - Novel reduction of indole-1-ketones to 1-alylindoles to 1-alkylindoles and mechanism of reduction of indole-1-aldehydes and ketones

Borane/THF reduction of nine indole-1-ketones (1a-1i) forms 1-ethylindoles (6a-6h) and the 1-benzylindole (6i) in 50-80percent yields.The ketones 1h and 1i, each of which bears phenyl groups at positions 2 and 3, also undergo deacylation to furnish 2,3-diphenylindole (8) in ca. 40percent yield.The mechanism of formation of both 8 and 6a-6i have been rationalised.The rate of borane/THF reduction of 1 is apparently slower than that of indole-1-carboxaldehydes (9).An attempt has been made to throw some light on the cause of this difference.