180479-96-3

Upstream product

• 2365-44-8 3-hydrazonoindolin-2-one 
• 59-48-3 2-oxoindole 
• 100-39-0 benzyl bromide 
• 476-34-6 isoindigo 
• 62-53-3 aniline 
• 42366-35-8 hydroxyimino-N-phenylacetamide 
• 91-56-5 indole-2,3-dione 
• 758640-21-0 N-Benzylaniline 
• 178809-24-0 (ortho-bromophenylacetyl)benzylamine 
• 18698-97-0 ortho-bromophenylacetic acid 
• 100-46-9 benzylamine 
• 7135-32-2 1-benzylindolin-2-one 
• 1217-89-6 1-benzylisatin 
• 74-88-4 methyl iodide 

Downstream Products

• 247061-37-6 C₃₄H₃₂N₈O 
• 180480-01-7 C₃₄H₃₆N₄O 
• 180479-99-6 C₃₄H₃₄N₂O₃ 
• 180480-03-9 (3aS,8aR,3'aR,8'aS)-8,8'-Dibenzyl-1,1'-dimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl] 
• 180480-02-8 (3aS,8aR,3'aR,8'aS)-8,8'-Dibenzyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl] 
• 180479-98-5 C₃₄H₃₀N₂O 
• 306944-74-1 C₃₇H₃₄N₂O₄ 
• 306944-72-9 C₃₇H₃₄N₂O₄ 
• 261350-20-3 1,1’-dibenzyl-3,3’-bis(2-hydroxyethyl)[3,3’-biindoline]-2,2’-dione 
• 582315-02-4 Trifluoro-methanesulfonic acid 2-{methyl-[(Z)-4-[methyl-(toluene-4-sulfonyl)-amino]-2-((3aS,8aS,3'aS,8'aR)-1,1',8'-trimethyl-2,3,8,8a,2',3',8',8'a-octahydro-1H,1'H-[3a,3'a]bi[pyrrolo[2,3-b]indolyl]-7-yl)-but-2-enoyl]-amino}-phenyl ester 
• 582315-05-7 (3S,3''S,3'aR,7'aR)-1-benzyl-1''-methyl-2',2'-dimethyl-3'a,4',7',7'a-tetrahydrospiro[3H-indole-3,5'(6'H)-[1,3]benzodioxole-6'-3''-[3H]indole]-2,2''-(1H,1''H)-dione 
• 616890-15-4 C₂₈H₂₆N₂O₄ 
• 582315-15-9 5-benzyl-(5aR,6aR,11bS,11cS)-bis(2-azidoethyl)-7-methyl-5,5a,6a,7-tetrahydrofuro[2,3-b:5,4-b']diindole 

Relevant academic research and scientific papers

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.

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

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.

Cyclization and oxidation of o-bromophenylacetamides for the synthesis of oxindoles and isoindigoes

N-substituted oxindoles were obtained through a facile KOH/DMSO promoted intramolecular cyclization of o-bromophenylacetamides in good yields. Furthermore, isoindigo derivatives were readily synthesized through sequential intramolecular cyclization, oxida

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.).

A cinchona alkaloid catalyzed enantioselective sulfa-Michael/aldol cascade reaction of isoindigos: Construction of chiral bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters

A cinchona alkaloid catalyzed diastereoselective and enantioselective sulfa-Michael/aldol cascade reaction between 1,4-dithiane-2,5-diol and isoindigos has been successfully developed to afford the highly congested bispirooxindole tetrahydrothiophenes with vicinal quaternary spirocenters in high yields (up to 91%), excellent diastereoselectivities (up to >20 : 1 dr), and good enantioselectivities (up to 98% ee). Some synthetic transformations of the reaction products were also studied.

Enantioselective synthesis of (-)-idiospermuline

The enantioselective total synthesis of the nonacyclic polypyrrolidinoindoline (-)-idiospermuline is described. Stereocontrolled formation of the vicinal quaternary carbon centers is achieved in a single step by dialkylation of an unsymmetrical prostereog