186093-84-5

Upstream product

• 3328-70-9 5-formyl-2-hydroxybenzaldehyde 
• 350-27-6 2-bromo-1-(3-fluoro-4-methoxyphenyl)ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 455-91-4 1-(3-fluoro-4-methoxyphenyl)ethanone 

Downstream Products

• 186093-95-8 5-[2-(3-Fluoro-4-methoxy-benzoyl)-benzofuran-5-ylmethyl]-thiazolidine-2,4-dione 

Relevant academic research and scientific papers

5-Formyl salicylaldehyde as a linker for the synthesis of benzofuran containing insulin sensitivity enhancer compounds

5-Formyl salicylaldehyde was prepared by treatment of 4-hydroxybenzaldehyde with HMTA in TFA. Reaction of this dialdehyde with α-haloacetyl aryl compounds gave 2,5-disubstituted benzofurans, from which an Insulin Sensitivity Enhancer compound was prepared.

Synthetic approaches to benzofuran containing Insulin Sensitivity Enhancer compounds for treatment of type II diabetes

The search for Insulin Sensitivity Enhancer (ISE) compounds, for potential use in the treatment of Type II diabetes, has led to the synthesis of compounds that contain a benzofuran spacer between an aryloyl substituent and a 2,4-thiazolidinedione pharmacophore. Sequential combination of haloacetyl aryl substrates with 5-formylsalicylaldehyde gave the desired 2-aryloyl-5-formylbenzofuran intermediates. A related class of compounds, those with a methylene tether between the aromatic moiety and the benzofuran spacer, were also prepared through this strategy.