35427-94-2

Upstream product

• 88-72-2 1-methyl-2-nitrobenzene 
• 100-52-7 benzaldehyde 
• 611-22-3 N-(o-tolyl)hydroxylamine 

Downstream Products

• 115879-44-2 3,4-Diphenyl-2-o-tolyl-[1,2,4]oxadiazolidin-5-one 
• 115879-45-3 3-Phenyl-2,4-di-o-tolyl-[1,2,4]oxadiazolidin-5-one 
• 115879-46-4 4-Naphthalen-1-yl-3-phenyl-2-o-tolyl-[1,2,4]oxadiazolidin-5-one 
• 1345509-85-4 ethyl 2,4-diphenyl-1-o-tolyl-1H-imidazole-5-carboxylate 
• 97369-40-9 (7-Methyl-2-indolyl)-3-phenylacrylnitril 
• 1185154-55-5 (±)-3-ethyl-7-methyl-3-phenylindolin-2-one 
• 1435517-47-7 (S,E)-N-(4-fluorobenzyl)-4-methyl-N-((3-phenyl-2-(o-tolyl)isoxazolidin-4-ylidene)methyl)benzenesulfonamide 
• 100-52-7 benzaldehyde 
• 91075-24-0 7-Methyl-2-(trichlormethylsulfinylmethyl)indol 
• 66625-55-6 (E)-1-methyl-2-(o-tolylimino)indolin-3-one 

Relevant academic research and scientific papers

Synthesis of Benzimidazolones via One-Pot Reaction of Hydroxylamines, Aldehydes, and Trimethylsilyl Cyanide Promoted by Diacetoxyiodobenzene

A novel and efficient PhI(OAc)2-promoted one-pot reaction of aromatic hydroxylamines, aldehydes, and TMSCN in the presence of BF3·Et2O is described. A wide variety of N-substituted benzimidazolones are obtained with satisfactory yields under mild reaction conditions. The method was proven to be efficient for the synthesis of benzimidazolone derivatives from readily available starting materials.

Synthesis of 2,3-Disubstituted NH Indoles via Rhodium(III)-Catalyzed C-H Activation of Arylnitrones and Coupling with Diazo Compounds

A rhodium-catalyzed intermolecular coupling between arylnitrones and diazo compounds by C-H activation/[4 + 1] annulation with a C(N2)-C(acyl) bond cleavage is reported, and 2,3-disubstituted NH indoles are directly synthesized in up to a 94% yield. A variety of functional groups are applicable to this reaction to give the corresponding products with high selectivity. Compared to other previously reported Rh(III)-catalyzed synthesis of homologous series, this method is simpler, more general, and more efficient.

An asymmetric pericyclic cascade approach to 3-alkyl-3-aryloxindoles: Generality, applications and mechanistic investigations

The reaction of L-serine derived N-arylnitrones with alkylarylketenes generates asymmetric 3-alkyl-3-aryloxindoles in good to excellent yields (up to 93%) and excellent enantioselectivity (up to 98% ee) via a pericyclic cascade process. The optimization, scope and applications of this transformation are reported, alongside further synthetic and computational investigations. The preparation of the enantiomer of a Roche anti-cancer agent (RO4999200) 1 (96% ee) in three steps demonstrates the potential utility of this methodology.

Asymmetric pericyclic cascade approach to spirocyclic oxindoles

The reaction of chiral N-arylnitrones with carbocyclic alkylarylketenes generates spirocyclic oxindoles in good yields and with excellent levels of enantioselectivity (90-99% ee) via a pericyclic cascade process.

Hetero-Cope Rearrangements, III. - Vinylindoles via Hetero-Cope Rearrangement

The reaction of N-phenylnitrones 1 with allenes 2 which are substituted with electron acceptor groups gives various products via addition and sigmatropic rearrangement depending on the specific acceptor group.In this manner one obtains 2-substituted indoles 8a, 8b, and 10 from propadienyl trichloromethyl sulfoxide.Using phenyl propadienyl sulfone a derivative 4a of tetrahydro-1-benzazepin-4-one is obtained.Reactions with allenecarbonitril proceed via several steps and yield 2-vinylindoles of type 6.Intermediate products could not be isolated.