33008-36-5

Upstream product

• 3096-63-7 N-(2,6-dimethylphenyl)hydroxylamine 
• 100-52-7 benzaldehyde 
• 81-20-9 2,6-dimethylnitrobenzene 
• 19064-77-8 C-phenyl-N-p-tolyl-nitrone 
• 97369-36-3 1,2,3,5-Tetrahydro-7-methyl-2-phenyl-3-phenylsulfonyl-4H-1-benzazepin-4-on 

Downstream Products

• 81724-84-7 N,N-dibenzoyl(2,6-dimethylphenyl)amine 
• 18109-39-2 N-(2,6-diimethylphenyl)benzamide 

Relevant academic research and scientific papers

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.

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.