2024
DOI: 10.1021/acs.joc.3c02042
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Vilsmeier–Haack-Initiated Formylative Rearrangement of Spirodioxo-lan-5-ones into Functionalized 4,5,6,7-Tetrahydrobenzofurans

Svetlana A. Varenichenko,
Victor Markov,
Jonas F. Goebel
et al.

Abstract: 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 POCl3 or PBr3 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 … Show more

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