180479-95-2

Upstream product

• 6011-63-8 3-hydroxy-1,3,1',3'-tetrahydro-[3,3']biindolyl-2,2'-dione 
• 59-48-3 2-oxoindole 
• 1261171-20-3 2-oxindole-3-thione S-oxide 
• 91-20-3 naphthalene 
• 7719-09-7 thionyl chloride 
• 7647-01-0 hydrogenchloride 
• 613-44-5 2-methoxyindol-3-one 
• 64-19-7 acetic acid 
• 56-23-5 tetrachloromethane 
• 91-56-5 indole-2,3-dione 
• 117069-75-7 3-aminoindolin-2-one 
• 7732-18-5 water 
• 16990-73-1 2-Hydroxyindole 
• 3526-43-0 N-(4-methoxybenzyl)aniline 

Downstream Products

• 97922-41-3 (E)-1,1'-dibenzhydryl-[3,3'-biindolinylidene]-2,2'-dione 
• 2365-44-8 3-hydrazonoindolin-2-one 
• 247061-40-1 (3S,3'S)-1,1'-dibenzyl-3,3'-bis-(2-hydroxyethyl)-[3,3'-biindoline]-2,2'-dione 
• 371252-55-0 2,2'-((3S,3'S)-1,1'-dibenzyl-2,2'-dioxo-[3,3'-biindoline]-3,3'-diyl)diacetaldehyde 

Relevant academic research and scientific papers

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.).

Mild and efficient synthesis of isoindigo derivatives catalyzed by Lewis acid

A mild and efficient ZrCl4-catalyzed synthesis of isoindigo derivatives from isatins and indolin-2-ones in refluxing ethanol is described. A variety of new functionalized isoindigo derivatives are obtained by simple filtration. Lewis acid was f

Acid-Catalyzed Rearrangements for a Diastereoselective Entry into a New Fused Hexacyclic Heterocycle: (5RS,7aRS,12RS,14aRS)-4,5,7,7a,11,12,14,14a-Octahydro-5,12-dimethyldiindonaphthyridine

The title compound 1 was obtained in 10.3percent overall yield via two acid-catalyzed rearrangements and pyrrolidine formation.Thus, bi-oxindole 6 afforded exclusively the thermodynamically stable cis-diazachrysene 7 which, after allylation, followed by aza-Claiser rearrangement gave alcohol 2.Pyrolytic ring clousere of the latter yielded 1 in a highly diastereoselective fashion.

Identification of an indigo precursor from leaves of Isatis tinctoria (Woad)

Indole is presumably a product of indole-3-glycerol phosphate catabolism in Isatis tinctoria. It is oxidized into indoxyl and stored in young leaves as indigo precursor. Further oxidation and dimerization of indoxyl produces indigoid pigments. In this work, we describe an HPLC method dedicated to the identification and quantification of indigoid pigments (indigo, indirubin, isoindigo and isoindirubin) and indigo precursors produced in I tinctoria (Woad). This work, carried out with two cultivars of I tinctoria, has confirmed that the quantity of indigo precursors is dependent on the species and the harvest period. In addition we have shown for the first time that young leaves of I. tinctoria, harvested in June contained a new indigo precursor in addition to isatan B (indoxyl-5-ketogluconate) and indican (indoxyl-β-D-glucoside). We suggest the name isatan C for this new indigo precursor in I. tinctoria. Its chemical characteristics point to an dioxindole ester with PM of 395. We have shown that isatan C reacts with isatan B increasing the red pigment production.

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-catalyzed asymmetric construction of vicinal all-carbon quaternary stereocenters and its application to the synthesis of cyclotryptamine alkaloids

A twofold Pd-DAAA Pd-catalyzed decarboxylative allylic alkylation (see scheme) was used to construct two vicinal all-carbon quaternary stereocenters (marked in red) in a diastereo- and enantioselective fashion. The products of the Pd-DAAA were further ela

Electroactive and photoactive poly[isoindigo-alt-EDOT] synthesized using direct (hetero)arylation polymerization in batch and in continuous flow

In this work, a combined approach was used to obtain a low-cost material for organic electronics by focusing on inexpensive monomers, short synthetic pathway, high-yielding polymerization method, low waste, and easy scalability. To achieve this, a new material, poly[isoindigo-alt-3,4-ethylenedioxythiophene], was synthesized using direct (hetero)arylation polymerization (DHAP). Only a few synthetic steps are required to obtain this material, and no organometallic intermediates are used. In order to make a bigger step toward a truly inexpensive technology, continuous flow methods were applied for the first time to DHAP. This method helped solving a common problem encountered in conjugated polymers synthesis, namely, batch-to-batch variations. Electronic properties of this polymeric material were evaluated using field effect transistors (μh = 7 × 10-3 cm2·V-1·s-1) and solar cells (η = 3.0%).

The first synthesis of cis-N,N′-dialkylisoindigo derivatives from 3-indolyl-2-oxindoles with DDQ

cis-N,N′-Dialkylisoindigo derivatives were synthesized for the first time by the reaction of 3-indolyl-2-oxindoles with DDQ in aqueous 1,4-dioxane. cis-Isoindigo derivatives were completely isomerized to the corresponding trans-isomers by heating the solu

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