36362-82-0

Basic information

• Product Name: 1H-Indole, 1,5-dimethyl-2,3-diphenyl-
• CAS NO: 36362-82-0
• Molecular Formula: C22H19N
• Molecular Weight: 297.4
• Mol File: 36362-82-0.mol

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 1,5-dimethyl-2,3-diphenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 1,5-dimethyl-2,3-diphenyl-(36362-82-0)
• EPA Substance Registry System: 1H-Indole, 1,5-dimethyl-2,3-diphenyl-(36362-82-0)

Safety Data

• Hazardous Substances Data: 36362-82-0(Hazardous Substances Data)

Upstream product

• 83824-13-9 5-methyl-2,3-diphenylindole-1-carboxaldehyde 
• 937-24-6 N-methyl-N-nitroso-p-toluidine 
• 501-65-5 diphenyl acetylene 
• 623-08-5 N-methyl-p-toluidine 
• 1610870-81-9 2-isobutylidene-1-methyl-1-(4-methylphenyl)hydrazine 
• 825-85-4 N,N-dimethyl-p-toluidine N-oxide 
• 24006-21-1 N-methyl-N-(4-tolyl)hydrazine 
• 886-38-4 diphenylcyclopropenone 

Relevant articles and documents

One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C-H Functionalization Sequence to Indole and Aniline Derivatives

The nitroso group served as a traceless directing group for the C-H functionalization of N-alkylanilines, ultimately removed after functioning either as an internal oxidant or under subsequent reducing conditions. The unique ability of o-NQ catalysts to aerobically oxidize the N-alkylanilines without using solvents and stoichiometric amounts of oxidants has rendered the new opportunity to develop the telescoped catalyst systems without a need for directly handling the hazardous N-nitroso compounds.

Divergent C-H activation synthesis of chalcones, quinolones and indoles

We here report a condition-controlled divergent synthesis strategy of chalcones, quinolones and indoles, which was achieved via a C-H activation reaction of N-nitrosoanilines and cyclopropenones. Variations of Ag salts are observed to be crucial for divergently constructing the three distinct chemical scaffolds. A Rh(i)- and Rh(iii)-cocatalyzed decarbonylation/C-H activation/[3+2] annulation cascade reaction was developed for the synthesis of indoles. These methodologies are characterized by mild reaction conditions, high functional group tolerance, and amenability to gram-scale synthesis, providing a reference for future derivation of new chemical scaffolds by C-H activation.

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.

Co(III)-Catalyzed, Internal and Terminal Alkyne-Compatible Synthesis of Indoles

A Co(III)-catalyzed, internal and terminal alkyne-compatible indole synthesis protocol is reported herein. The N-amino (hydrazine) group imparts distinct, diverse reactivity patterns for directed C-H functionalization/cyclization reactions. Notable synthetic features include regioselectivity for a meta-substituted arylhydrazine, regioselectivity for a chain-branched terminal alkyne, formal incorporation of an acetylenic unit through C2-desilylation on a C2-silylated indole derivative, formal inversion of regioselectivity through consecutive C3-derivatization and C2-desilylation processes, and formal bond migration for a linear-chain terminal alkyne.

Cationic Cobalt(III) Catalyzed Indole Synthesis: The Regioselective Intermolecular Cyclization of N-Nitrosoanilines and Alkynes

The unique regioselectivity and reactivity of cobalt(III) in the direct cyclization of N-nitrosoanilines with alkynes for the expedient synthesis of N-substituted indoles is demonstrated. In the presence of a cobalt(III) catalyst, high regioselectivity was observed when using unsymmetrical meta-substituted N-nitrosoanilines. Moreover, internal alkynes bearing electron-deficient groups, which are almost unreactive in the [Cp?RhIII]-catalyzed system, display good reactivity in this transformation.

Rh(III)-catalyzed chemoselective C-H functionalizations of tertiary aniline: N -oxides with alkynes

In this work, we report novel Rh(iii)-catalyzed chemoselective functionalizations of tertiary aniline N-oxides with alkynes, including annulation via the sequential C(sp2)-H and C(sp3)-N activation for the formation of N-alkylindoles and an O-atom transfer (OAT) process for the synthesis of acetophenones.

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.

Rhodium(III)-catalyzed synthesis of indoles from 1-alkylidene-2- arylhydrazines and alkynes via C-H and N-N bond cleavages

1-Alkylidene-2-arylhydrazines undergo annulative coupling with internal alkynes in the presence of a rhodium(III) catalyst and a copper(II) salt. The reaction proceeds through cleavage of the C-H and N-N bonds of hydrazines to afford 1,2,3-trisubstituted indole derivatives.

Traceless directing strategy: Efficient synthesis of N-alkyl indoles via redox-neutral C-H activation

A general protocol for the synthesis of N-alkyl indoles has been developed via a redox neutral C-H activation strategy using a traceless nitroso directing group. A broad scope of substituted N-alkyl indoles has been prepared in good to excellent yields using a very simple Rh catalyst system in the absence of an external oxidant or any other additive. Good to excellent regioselectivity has been achieved for asymmetrically disubstituted acetylenes.

DIBORANE AS A REDUCING AGENT - VI. THE NOVEL REDUCTION OF INDOLE-1-CARBOXALDEHYDES TO 1-METHYL-INDOLES, DI(INDOLYLMETHYL)ETHERS AND INDOLYLMETHYL INDOLINES

Reduction of the indole-1-carboxaldehydes (1a-1f) with borane/THF gives the 1-methylindoles (4) in 42-91 percent yields together with the di(indolylmethyl)ethers (8), the indolylmethyl indolines (7), the unsymmetric ether (10) and the indolenine (11) as the minor products, except 7a.This appears to be the first report on the formation of symmetric ethers in the borane/THF reduction of an oxygen function.The formation of 7a and 7b from 1a and 1b implies that electrophilic substitution takes place primarily at position 3 of 3-substituted indoles. 1c-1f did not form the corresponding 7 probably because of steric hindrance.These results are discussed in relation to the mechanisms of borane/THF reduction, origin of the different products and electrophilic substitution in 3-substituted indoles.