Facile entry into structurally diverse, privileged, (hetero)arene-fused N-alkoxy 3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-ones

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• 作者：Alexander Sapegin^a ; Elena Reutskaya^b ; Alexey Smirnov^b ; Mikhail Korsakov^b ; Mikhail Krasavin^a ; ^{m.krasavin@spbu.ru}
• 关键词：Tandem cyclization ; Nucleophilic aromatic substitution ; Smiles rearrangement ; Tricyclic scaffolds ; Benzo[1 ; 4]oxazepines ; Privileged structures ; Lossen rearrangement
• 刊名：Tetrahedron Letters
• 出版年：2016
• 出版时间：28 December 2016
• 年：2016
• 卷：57
• 期：52
• 页码：5877-5880
• 全文大小：2226 K
• 卷排序：57

文摘

Rare tricyclic N-alkoxy benzo[1,4]oxazepines synthesized via a novel strategy. Involves a tandem SNAr – Smiles rearrangement – SNAr process. O-Alkyl hydroxamic acids react with bis-electrophilic (hetero)aromatic compounds. N-Hydroxy compounds can be obtained by O-dealkylation. Free hydroxamic acids do not react in the same way and undergo Lossen rearrangement.