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La(OTf)3‐Mediated [3+3]‐Annulation of Benzoxepines and Aminocrotonates: Easy Access to Bridged Bicyclic Benzoxepine Heterocycles

A new and effective method for making bridged bicyclic benzoxepine derivatives were devised through the intermolecular [3+3]‐annulation of benzoxepine‐3‐carboxylates with aminocrotonates in the presence of La(OTf)3. The compounds were formed… Click to show full abstract

A new and effective method for making bridged bicyclic benzoxepine derivatives were devised through the intermolecular [3+3]‐annulation of benzoxepine‐3‐carboxylates with aminocrotonates in the presence of La(OTf)3. The compounds were formed through reactions involving the benzoxepine moiety's C‐3 and C‐5 carbons to produce C‐C and C‐N bonds. One of the compound structure (±) 12‐ethyl‐6‐methyl‐3‐hydroxy‐5‐methyl‐2,3,4,7‐tetrahydro‐3,7‐methano benzo[h][1,4]‐oxazonine‐6,12‐dicarboxylate was confirmed by single crystal X‐ray analysis.

Keywords: bridged bicyclic; bicyclic benzoxepine; mediated annulation; otf mediated; benzoxepine

Journal Title: European Journal of Organic Chemistry
Year Published: 2024

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