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

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• 作者：Kseniya Karamysheva^a ; Elena Reutskaya^a ; Alexander Sapegin^a ; Mikhail Dorogov^a ; Mikhail Krasavin^b ; ^{m.krasavin@spbu.ru" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Imidazoline arylation ; Monoamine uptake inhibitors ; Polycyclic aromatic scaffolds ; Smiles rearrangement ; Nucleophilic aromatic substitution ; Regiospecificity
• 刊名：Tetrahedron Letters
• 出版年：2015
• 出版时间：7 October 2015
• 年：2015
• 卷：56
• 期：41
• 页码：5632-5636
• 全文大小：3451 K

文摘

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.