58421-67-3

Upstream product

• 88-74-4 2-nitro-aniline 
• 603-76-9 1-methylindole 
• 609-73-4 o-nitroiodobenzene 
• 577-19-5 2-nitrophenyl bromide 
• 1365647-62-6 C₂₃H₃₀N₂O₂Si 
• 208655-73-6 (1-(triisopropylsilyl)-1H-indol-3-yl)boronic acid 
• 56366-31-5 3-(2-nitrophenyl)-1H-indole 
• 74-88-4 methyl iodide 
• 148249-36-9 3-bromo-1-(1,1,1-triisopropylsilyl)-1H-indole 
• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 120-72-9 indole 

Downstream Products

• 1431882-11-9 5-methyl-6-tosyl-5,6-dihydroindolo[2,3-b]indole 
• 857800-26-1 2-(1-methyl-1H-indol-3-yl)aniline 

Relevant academic research and scientific papers

Ascorbic Acid as an Aryl Radical Inducer in the Gold-Mediated Arylation of Indoles with Aryldiazonium Chlorides

In recent years interest in the development of protocols that facilitate the oxidative addition of gold to access mild cross-coupling processes mediated by this metal has increased. In this context, we report herein that ascorbic acid, a natural and readily accessible antioxidant, can be used to accelerate the oxidative addition of aryldiazonium chlorides onto AuI. The aryl–AuIII species generated in this way, has been used to prepare 3-arylindoles in a one-pot protocol starting from anilines and para-, meta-, and ortho- substituted aryldiazonium chlorides. The mechanism underlying the oxidative addition has been examined in detail based on EPR analyses, cyclic voltammetry, and DFT calculations. Interestingly, we have found that in this protocol, the chloride atom induces the AuII/AuIII oxidation step.

Metal-Free Synthesis of Pyrrolo[1,2- a ]quinoxalines Mediated by TEMPO Oxoammonium Salts

We herein describe a novel TEMPO oxoammonium salt initiated Pictet-Spengler reaction of imines, generated in situ from carbonyl compounds and pyrrole- or indole-containing substrates, to afford 4,5-dihydropyrrolo[1,2- a ]quinoxalines or 5,6-dihydroindolo[1,2- a ]quina-oxalines in good to excellent yields. Moreover, a one-pot synthesis of a biologically important quinoxaline is achieved via a cyclization-dehydrogenation process using one equivalent of the oxoammonium salt.

Iodine mediated intramolecular C2-amidative cyclization of indoles: A facile access to indole fused tetracycles

A novel and metal-free I2-mediated intramolecular C2 amidation of indoles under mild reaction conditions is developed. This methodology affords various indole fused tetracyclic compounds, such as benzo[4,5]imidazo[1,2-a]indoles by intramolecular C2 amidation of N-aryl substituted indoles. This C2 sulfonamidative cyclization also offers convenient access to indolo[2,3-b]indoles and dihydroindolo[2,3-b]quinoline from C3 aryl substituted indoles in good to excellent yields. Indolo[2,3-b]quinolines are also synthesized by the domino cyclization-detosylation-aromatization reaction sequence.

Iodine-Mediated Intramolecular Dehydrogenative Coupling: Synthesis of N-Alkylindolo[3,2-c]- and -[2,3-c]quinoline Iodides

An I2/TBHP-mediated intramolecular dehydrogenative coupling reaction is developed for the synthesis of a library of medicinally important 5,11-dialkylindolo[3,2-c]quinoline salts and 5,7-dimethylindolo[2,3-c]quinoline salts. The annulation reaction is followed by aromatization to yield tetracycles in good yield. This protocol is also demonstrated for the synthesis of the naturally occurring isocryptolepine in salt form.

NITROGENATED AROMATIC COMPOUND, ORGANIC SEMICONDUCTOR MATERIAL, AND ORGANIC ELECTRONIC DEVICE

Provided are a nitrogen-containing aromatic heterocyclic compound useful as an organic semiconductor material and an organic electronic device using this compound. The nitrogen-containing aromatic heterocyclic compound has a fused indole skeleton represented by the following formula (1), the organic semiconductor material contains the said compound, and the organic electronic device uses the said organic semiconductor material. In general formula (1), X is N-A', O, S, or Se; A is an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more; and R is a hydrogen atom, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or an aromatic heterocyclic group exclusive of a fused heterocycle consisting of 4 rings or more.