Atom-economical construction of tetracyclic [1,4]oxazepines involving intramolecular arylation of a 2-imidazoline moiety

作者：Karamysheva Kseniya; Reutskaya Elena; Sapegin Alexander; Dorogov Mikhail; Krasavin Mikhail^*

来源：Tetrahedron Letters, 2015, 56(41): 5632-5636.

DOI：10.1016/j.tetlet.2015.08.062

• Imidazoline arylation
• Monoamine uptake inhibitors
• Polycyclic aromatic scaffolds
• Smiles rearrangement
• Nucleophilic aromatic substitution
• Regiospecificity

Novel [1,4]oxazepines containing a fused imidazoline moiety were synthesized from 2-hydroxyphenyl imidazolines and bis-electrophilic aromatic substrates in a reaction involving sequential nucleophilic aromatic substitution steps and a Smiles rearrangement. A notable step was the remarkably facile, metal-free intramolecular N-arylation of the imidazoline moiety with a fluoro-, nitro- or chloroaromatic or heteroaromatic ring. The approach presented in this Letter not only details access to a new, medicinally relevant tetracyclic [1,4]oxazepine core but also extends the scope of imidazoline arylation chemistry.

• 出版日期2015-10-7