476-34-6

Usage

Uses

Used in Organic Electronics:
Isoindigotin is used as an electron-accepting building block for the preparation of electroactive materials in organic electronics. Its electronic properties make it a promising candidate for the development of new materials with improved performance in electronic devices.
Used in Pharmaceutical Industry:
Isoindigotin is used as an indirubin substitute for the treatment of chronic myeloid leukemia (CML). Meisoindigo, a functionalized form of isoindigotin, has shown potential in this application, offering an alternative treatment option for patients with this type of cancer.

InChI:InChI=1/C16H10N2O2/c19-15-13(9-5-1-3-7-11(9)17-15)14-10-6-2-4-8-12(10)18-16(14)20/h1-8H,(H,17,19)(H,18,20)/b14-13+

Upstream product

• 59-48-3 2-oxoindole 
• 91-56-5 indole-2,3-dione 
• 6011-63-8 3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione 
• 56-81-5 glycerol 
• 61-71-2 dioxindol 
• 1261171-20-3 2-oxindole-3-thione S-oxide 
• 62-53-3 aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 6326-79-0 6-bromoisatin 
• 99365-40-9 6-bromo-2,3-dihydro-1H-indole-2-one 
• 103-84-4 Acetanilid 
• 21905-78-2 N-acetyloxindole 
• 33333-60-7 3-hydroxy-3-indolyl-2-oxindole 
• 120-72-9 indole 

Downstream Products

• 6011-63-8 3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione 
• 91-56-5 indole-2,3-dione 
• 1198772-90-5 1-(p-hydroxy-phenethyl)-isoindigo 
• 1198772-91-6 1-(p-nitro-phenethyl)isoindigo 
• 1198772-87-0 1-(phenpropyl)-isoindigo 
• 1198772-92-7 1-(p-acetylamino-phenethyl)-isoindigo 
• 1380315-91-2 C₂₉H₃₄N₄O₇ 
• 1380315-89-8 C₃₃H₄₂N₄O₆ 
• 595-05-1 (4bR,5S,10bR,11S)-13,18-dimethyl-5,6,11,12-tetrahydro-5,10b:11,4b-bis(epiminoethano)dibenzo[c,h][2,6]naphthyridine 

Relevant academic research and scientific papers

COS-triggered oxygen/sulfur exchange of isatins: Chemoselective synthesis of functionalized isoindigos and spirothiopyrans: Via self-condensation and the thio-Diels-Alder reaction

Herein, we present the first organocatalytic oxygen/sulfur atom exchange reaction (O/S ER) of isatins by employing carbonyl sulfide (COS) as a novel sulfuring reagent under mild reaction conditions. 8-Diazabicyclo[5.4.0]undec-7-ene (DBU) exhibited excellent activity in this approach. Remarkably, the chemical transformations of in situ generated 3-thioisatins can be tuned via the judicious choice of reaction solvents in a one pot process, enabling the selective formation of either functionalized isoindigos in CH3CN via a self-condensation process or spirothiopyrans in DMSO in the presence of conjugated dienes via the thio-Diels-Alder reaction. Mechanistic studies with experimental and density functional theory approaches revealed that the O/S ER between isatins and COS results in the formation of 3-thioisatins as the key intermediates, which further undergo solvent-controlled transformations to generate isoindigos or spirothiopyrans, respectively. The easily-accessible substrates and operational simplicity make the process suitable for further exploration. The practicality of this transformation was demonstrated by the gram-scale synthesis of isoindigo-based drug molecules and donor-acceptor conjugated polymers. This journal is

Method for preparing isoindigo compound by organically catalyzing isatin self-condensation

The invention discloses a method for preparing an isoindigo compound by organically catalyzing isatin self-condensation, which relates to the technical fields of organic synthesis, dyes, pharmaceutical chemicals, organic photoelectric materials and the li

Perfluorobutyl substituted compound as well as preparation method and application thereof (by machine translation)

The invention discloses a perfluorobutyl substituted compound as well as a preparation method and application; and a preparation method and application thereof. The chemical structural formula of the compound is as shown in formula (III), (VI), (X), wherein R is a branched alkane or a straight-chain alkane having 8~16 carbon atoms, and the compound has better dissolving performance, and the yield of each step is higher than the unitunityl ?. 10%. There is better air stability compared to compounds which are not substituted with fluoroalkyl groups, for example. The LUMO, HOMO energy level and the like are reduced, so that electron injection and transmission, and the maximum absorption wavelength in the field, of organic field effect transistors (OFET), organic solar cells (OPV), have potential application prospects. (by machine translation)

Organo-Cation Catalyzed Asymmetric Homo/Heterodialkylation of Bisoxindoles: Construction of Vicinal All-Carbon Quaternary Stereocenters and Total Synthesis of (-)-Chimonanthidine

A novel chiral spirocyclic amide (SPA)-derived triazolium organocatalyst has been designed and demonstrated to effect asymmetric homo- and heterodialkylations of various bisoxindoles, enabling enantioselective construction of vicinal all-carbon quaternary stereocenters. These reactions feature excellent enantio- and diastereoselectivities (up to 99% ee and >20:1 dr) as well as good to high yields (up to 89% over two steps). As an application of this methodology, the first asymmetric total synthesis of (-)-chimonanthidine has been achieved.

Gold(I)-Catalyzed Dimerization of 3-Diazooxindoles towards Isoindigos

A gold-catalyzed dimerization of 3-diazooxindoles was developed, delivering isoindigos as products. The reaction shows broad substrate scope and functional group tolerance by affording various substituted isoindigos. Moreover, the method also exhibited high efficiency on a gram-scale reaction.

NaI-mediated divergent synthesis of isatins and isoindigoes: A new protocol enabled by an oxidation relay strategy

A new approach for the synthesis of isatins and isoindigoes by an inexpensive and environmentally friendly NaI-mediated transformation is disclosed. The selectivity could be switched by simply varying the solvent, and isatins (using THF) and isoindigoes (using DMSO) could be obtained in moderate to excellent yields.

Synthesis of oxindole from acetanilide via Ir(iii)-catalyzed C-H carbenoid functionalization

Herein we disclose the first report on the synthesis of oxindole derivatives from acetanilide via Ir(iii)-catalyzed intermolecular C-H functionalization with diazotized Meldrum's acid. A broad range of substituted anilides were found to react smoothly under the Ir(iii)-catalytic system to afford the corresponding N-protected oxindoles. The N-protecting groups, such as Ac, Bz or Piv, can be easily removed to furnish the oxindole. Various synthetic applications of the synthesized oxindole were also demonstrated.

Synthesis of 2-Oxindoles Sharing Vicinal All-Carbon Quaternary Stereocenters via Organocatalytic Aldol Reaction

An organocatalytic enantioselective aldol reaction using paraformaldehyde as C1-unit has been developed for the synthesis of 2-oxindoles sharing vicinal all-carbon quaternary stereocenters. The methodology is eventually employed in the formal total synthesis of (+)-folicanthine (1b).

Palladium(II) Acetate-Catalyzed Dual C–H Functionalization and C–C Bond Formation: A Domino Reaction for the Synthesis of Functionalized (E)-Bisindole-2-ones from Diarylbut-2-ynediamides

A domino reaction of palladium(II)-catalyzed dual C–H functionalization with subsequent intramolecular annulation is presented. This method provides a convenient synthesis of a range of symmetrical and unsymmetrical biologically important (E)-bisindole-2-ones under extremely mild reaction conditions – room temperature, green oxidant and no additive. The reaction mechanism is elucidated in light of the yield values as well as additional control experiment results. (Figure presented.).