17017-60-6

Upstream product

• 91-55-4 2,3-dimethylindole 
• 126920-20-5 cis-1-Benzyl-2,3-dimethyl-2,3-dihydroindole 
• 60011-48-5 N-benzyl-N-(3-methyl-2-butyne)aniline 
• 1152163-62-6 C₁₀H₁₀BrN 
• 100-39-0 benzyl bromide 
• 944722-06-9 2-(1-methylpropa-1,2-dien-1-yl)-N-(phenylmethyl)aniline 
• 758640-21-0 N-Benzylaniline 
• 3355-28-0 1-Bromo-2-butyne 
• 1217-89-6 1-benzylisatin 
• 75-16-1 methylmagnesium bromide 
• 22120-50-9 2,3-dimethyl-2,3-dihydro-1H-indole 
• 59-88-1 phenylhydrazine hydrochloride 

Downstream Products

• 1435466-95-7 C₃₁H₃₃NO₅ 

Relevant academic research and scientific papers

Molybdenum-catalyzed α-hydrostannations of propargylamines as the key step in the synthesis of N-heterocycles

The Mo-catalyzed hydrostannation of propargylic amines and amides gave rise to functionalized vinylstannanes in good yield. The α-stannylated products were formed preferentially, which are interesting synthetic building blocks. If halogenated aromatic ami

One-pot, three-component Fischer indolisation-N-alkylation for rapid synthesis of 1,2,3-trisubstituted indoles

A one-pot, three-component protocol for the synthesis of 1,2,3-trisubstituted indoles has been developed, based upon a Fischer indolisation-indoleN-alkylation sequence. This procedure is very rapid (total reaction time under 30 minutes), operationally straightforward, generally high yielding and draws upon readily available building blocks (aryl hydrazines, ketones, alkyl halides) to generate densely substituted indole products. We have demonstrated the utility of this process in the synthesis of 23 indoles, benzoindoles and tetrahydrocarbazoles bearing varied and useful functionality.

Synthesis of stereochemically-biased spiropyrans by microwave-promoted, one-pot alkylation-condensation

A microwave-assisted, two-step, one-pot synthesis of spiropyrans has been developed. This process was used to synthesise a range of sterically-congested spiropyrans from readily available precursors, employing environmentally benign solvents. The unusual substituent pattern possessed by these structures has been shown to influence the stereoselectivity of spiropyran ring-closure.

Frustrated Lewis Pair Catalyzed Dehydrogenative Oxidation of Indolines and Other Heterocycles

An acceptorless dehydrogenation of heterocycles catalyzed by frustrated Lewis pairs (FLPs) was developed. Oxidation with concomitant liberation of molecular hydrogen proceeded in high to excellent yields for N-protected indolines as well as four other substrate classes. The mechanism of this unprecedented FLP-catalyzed reaction was investigated by mechanistic studies, characterization of reaction intermediates by NMR spectroscopy and X-ray crystal analysis, and by quantum-mechanical calculations. Hydrogen liberation from the ammonium hydridoborate intermediate is the rate-determining step of the oxidation. The addition of a weaker Lewis acid as a hydride shuttle increased the reaction rate by a factor of 2.28 through a second catalytic cycle.

Facile regiospecific synthesis of 2,3-disubstituted indoles from isatins

A facile regiospecific synthesis of 2,3-disubstituted indoles from isatins has been developed. Nucleophilic addition of Grignard reagents to commercially available isatins, followed by reduction with borane, afforded an array of structurally diverse 2,3-disubstituted indoles in moderate to good yields. The method described herein represents a novel and very simple approach to synthesize various 2,3-disubstituted indoles, extremely important structural motifs in the pharmaceutical industry and medicinal chemistry. This journal is the Partner Organisations 2014.

Rhodium(I)-catalyzed synthesis of indoles: Amino-claisen rearrangement of N-propargylanilines

Mild and facile preparations of 2-substituted or 2,3-disubstituted indole compounds were achieved by RhH(CO)(Ph3P)3 (4-10 mol %)-catalyzed reaction of N-propargylanilines in hexafluoroisopropyl alcohol (HFIP). The formation of indole

Synthesis of 2,3-disubstituted indoles by a rhodium-catalyzed aromatic amino-claisen rearrangement of N-propargyl anilines

(Chemical Equation Presented) Give me a ring! A cationic RhI catalyst promotes the formation of fused arenes containing a five-membered ring (see scheme) by an aromatic amino-Claisen rearrangement of N-propargyl aniline derivatives in refluxing

One-Pot Synthesis of Indoles from 1-Benzyl-2,3-dihydroindoles

A facile one-pot dehydrodebenzylation of 1-benzyl-2,3-dihydroindoles to indoles uses 10percent palladium on carbon as catalyst and ammonium formate as hydrogen donor in methanol.