1136423-27-2

Upstream product

• 86255-43-8 trans-1-(3,5-Dimethoxyphenyl)-2-nitroethylene 
• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 3213-28-3 3,5-dimethoxyphenethylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1428536-55-3 7,9-dimethoxy-3-(p-toluenesulfonyl)-1-vinyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine 

Relevant academic research and scientific papers

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

Synthesis of 3-benzazepines and azepino[4,5-b]heterocyclic ring systems via intramolecular Friedel-Crafts cyclization

The intramolecular Friedel-Crafts cyclization was found to be effective for the synthesis of 3-benzazepines and azepino[4,5-b]heterocyclic ring systems using simple allylic bromides tethered to activated aromatic nuclei. Amongst the various Lewis acids screened, Bi(OTf)3 was found to be the most effective 'ecofriendly' catalyst for the cyclization.