39212-30-1

Upstream product

• 108-94-1 cyclohexanone 
• 82757-20-8 N-[2-(1-hydroxycyclohexyl)phenyl]formamide 
• 10113-38-9 N-(2-bromophenyl)formamide 
• 59816-86-3 1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-amine 
• 46175-80-8 2‘,3‘,4‘,5‘-tetrahydro-[1,1‘-biphenyl]-2-amine 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 106795-52-2 1-(2-aminophenyl)cyclohexan-1-ol 

Downstream Products

• 923291-49-0 (Z)-phenyl N-[2-(cyclohexen-1-yl)phenyl]ethaneselenoimidate 
• 474817-83-9 6-(2-acetamidophenyl)-6-oxohexanoic acid 

Relevant academic research and scientific papers

Cyclization of N-acetyl-ortho-cycloalkenylanilines on treatment with bromine and N-bromosuccinimide

The reaction of N-acetyl-2-(cyclohex-1-enyl)aniline with Br2 or N-bromsuccinimide at 20 °C is accompanied by intramolecular cyclization to give brominated 3,1-benzoxazines or 4-acetyl-3-bromo-5-methyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole.

Two New Oxindole Syntheses

Two oxindole syntheses are described, both starting from ketones, in which the carbonyl carbon becomes C-3 of the oxindole.The first route uses o-lithioformanilide followed by attack with cyanide ion and hydrolysis.The second uses a pinacol-type rearragement (or the γ-silyl alcohol variation) to create the quaternary centre, and involves an intramolecular displacement of fluoride ion from an unactivated benzene ring by an amide nitrogen to complete the lactam ring.The two routes are stereochemically complementary, giving different spiro-oxindoles from norbornanone.