1244651-60-2

Upstream product

• 1244651-37-3 N-(3-bromo-2-iodophenyl)-2-hydroxy-2-methylpropanamide 
• 693-02-7 hex-1-yne 
• 450412-22-3 1-bromo-2-iodo-3-methoxybenzene 
• 855836-52-1 3-bromo-2-iodophenol 
• 2398-37-0 3-methoxyphenyl bromide 
• 1287791-68-7 2-(3-bromo-2-iodophenoxy)-2-methylpropanamide 
• 863870-79-5 O-3-bromo-2-iodophenyl N,N-diethylcarbamate 
• 863870-72-8 O-3-bromophenyl N,N-diethylcarbamate 

Downstream Products

• 1287792-08-8 4-bromo-2-butyl-3-(phenylthio)-1H-indole 
• 1287792-10-2 2-butyl-4-phenyl-1H-indole 

Relevant academic research and scientific papers

Construction of Tricyclic Nitrogen Heterocycles by a Gold(I)-Catalyzed Cascade Cyclization of Allenynes and Application to Polycyclic π-Electron Systems

A novel approach to the direct construction of tricyclic nitrogen heterocycles based on gold-catalyzed cascade cyclization of aminoallenynes is described. The expected biscyclization reaction of hydroxyisobutyryl-protected aminoallenynes was efficiently promoted by a catalytic amount of BrettPhosAuNTf2 in the presence of iPrOH to produce 1,2-dihydrobenzo[cd]indole derivatives in good yields. When the reaction was combined with Friedel–Crafts acylation or palladium-catalyzed N-arylation, the resulting tricyclic products were efficiently converted into nitrogen-containing polycyclic aromatic compounds (N-PACs) with highly conjugated π-electron systems. A newly obtained hexacyclic indolium salt showed characteristic concentration-dependent absorption and emission properties.

Approaches to the synthesis of 2,3-dihaloanilines. Useful precursors of 4-functionalized-1 H-indoles

2,3-Dihaloanilines have been proved as useful starting materials for synthesizing 4-halo-1H-indoles. Subsequent or in situ functionalization of the prepared haloindoles allows the access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles in good overall yields. As no efficient synthetic routes to 2,3-dihaloanilines have been described in the literature, different approaches to the preparation of these 1,2,3-functionalized aromatic precursors are now presented. The most general one involves a Smiles rearrangement from the corresponding 2,3-dihalophenols and allows the preparation of 2,3-dihaloanilides in a straightforward and synthetically useful manner.

Synthesis of 4-functionalized-1H-indoles from 2,3-dihalophenols

A new synthesis of 4-halo-1H-indoles has been developed from easily available 2,3-dihalophenol derivatives. The key steps are Smiles rearrangement and a one-pot or stepwise Sonogashira coupling/NaOH-mediated cyclization. Subsequent functionalization allows access to a wide variety of 2,4- or 2,3,4-regioselectively functionalized indoles.