23206-21-5

Upstream product

• 615-43-0 2-iodophenylamine 
• 5339-85-5 2-aminophenethyl alcohol 
• 552-89-6 2-nitro-benzaldehyde 
• 579-71-5 2-nitrostyrene 
• 92988-08-4 trivinylboroxin 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 3867-18-3 2-vinylaniline 
• 79-22-1 methyl chloroformate 

Downstream Products

• 39203-20-8 methyl 1H-indole-1-carboxylate 
• 143952-53-8 methyl 2-methyl-1H-indole-1-carboxylate 
• 911022-76-9 methyl (1-methylethenyl)(2-vinylphenyl)carbamate 

Relevant academic research and scientific papers

Oxidative Route to Indoles via Intramolecular Amino-Hydroxylation of o-Allenyl Anilines

A new intramolecular oxidative amino-hydroxylation of o-allenyl anilines is reported. Treatment of carbamate-protected anilines with lead(IV) carboxylates in dichloromethane at room temperature results in facile tandem C-N (allene cyclization) and C-O bon

Pd-tBuONO Cocatalyzed Aerobic Indole Synthesis

A Pd-tBuONO co-catalyzed scalable and practical synthesis of indoles with molecular oxygen as terminal oxidant is developed. Either terminal or internal 2-vinylanilines could be smoothly converted to desired indoles under one general condition. This method has been evaluated in the large scale synthesis of indomethacin and a potential anti-breast cancer drug candidate 1. (Figure presented.).

Indole synthesis based on a modified koser reagent

A new metal-free method for the rapid and productive preparation of indoles has been developed. This process is based on sterically congested hypervalent iodine compounds of the family of Koser reagents, and iodosobenzene in combination with 2,4,5-tris-isopropylbenzene sulfonic acid provides the highest yields and fastest reaction times. This reagent alone promotes the chemoselective oxidative cyclization of 2-amino styrenes to indoles in high yields under mild conditions. Convenient route to indole: A fast, productive, and operationally simple indole synthesis was developed.

Pd-catalyzed arylation/ring-closing metathesis approach to azabicycles

Palladium-catalyzed arylation followed by Grignard addition to imines and ring-closing metathesis, using Grubbs' catalysts, provides a route to six-, seven-, and eight-membered azabicycles.

Sequential N-acylamide methylenation-enamide ring-closing metathesis: Construction of benzo-fused nitrogen heterocycles

The dimethyltitanocene methylenation of N-acylamides derived from ortho-vinylanilines, ortho-allylaniline, and ortho-vinylbenzylamine provides the corresponding enamides, which upon exposure to the second generation Grubbs ruthenium catalyst give access to indoles, 1,4-dihydroquinolines, and 1,2-dihydroisoquinolines, respectively. This sequential protocol also allows the synthesis of dihydrobenzoazepines, although the ring-closing metathesis (RCM) step is complicated by the alkene isomerization processes. From certain substrates, the direct annulation is observed in the titanium-mediated step, which is likely to occur through an olefin metathesis-intramolecular olefination sequence.