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Vilsmeier-Haack-Initiated Formylative Rearrangement of Spirodioxo-lan-5-ones into Functionalized 4,5,6,7-Tetrahydrobenzofurans.

Svetlana A VarenichenkoVictor MarkovJonas F GoebelLukas J GooßenOleg K Farat
Published in: The Journal of organic chemistry (2024)
Pharmaceutically relevant bicyclic furans can be synthesized in a single step from substituted dioxolan-5-ones by reacting with Vilsmeier-Haack reagents. These reagents are generated from POCl 3 or PBr 3 and DMF. The reaction cascade is mechanistically complex and involves deoxyhalogenation, iminomethylation, and electrophilic rearrangement steps, which are facilitated by the DMF solvent. The synthesis of hard-to-access 4,5,6,7-tetrahydrobenzofurans and substituted aliphatic furans is particularly useful. These compounds are potential isosteres of 2,3-dihydrobenzofuran pharmacophores and could be of interest for drug discovery.
Keyphrases
  • drug discovery
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  • human health
  • molecular dynamics simulations
  • risk assessment
  • molecularly imprinted
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  • high resolution
  • electron transfer