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Synthesis of 2,3,4,5-Tetrahydro-1,5-benzoxazepine Derivatives via Alkoxy Migration Induced by N–O Bond Cleavage of N-Aryl Isoxazolidines

Year: 2026

Type: article

Abstract: 2,3,4,5-Tetrahydro-1,5-benzoxazepine derivatives constitute an important class of heterocycles frequently found in pharmaceuticals. In this study, we developed an efficient and practical synthetic method for the construction of 2,3,4,5-tetrahydro-1,5-benzoxazepine cores starting from N-aryl isoxazolidines. The key step involves Lewis acid-mediated alkoxy migration induced by N-O bond cleavage using aluminum chloride, providing the desired heterocyclic scaffolds in good yields. This method offers a new route to access 2,3,4,5-tetrahydro-1,5-benzoxazepine frameworks and expands the utility of N-aryl isoxazolidines in heterocycle synthesis.

Source: Chemical and Pharmaceutical Bulletin

DOI: 10.1248/cpb.c26-00150

Authors: Kosaku Tanaka III, Motoko Nishidate, Hitomi Chiaki, Yoshimitsu Hashimoto, Nobuyoshi Morita, Osamu Tamura

Institutions: Hokkaido University, Showa Pharmaceutical University

Language: English

Topic: Chemical synthesis and pharmacological studies

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: diamond

OpenAlex ID: W7165195390

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