A DFT Study on the Mechanism of Selective Formation of Substituted Azepines From 1-Azabutadienes and Cyclopropanes.

Ryo Kobayashi, Chao Wang, Shuto Kosuge, Yuji Matsuya, Kenji Sugimoto, Keiichi Hirano

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In one paragraph

Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

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1 citing paper in PubMed.

Formal [1,5] Rearrangement of Cyclopropanone Hemiaminals: Synthesis of Tetrahydrobenzazepinone Derivatives.Organic letters · 2026
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Authors and funding

6 authors.

Ryo KobayashiInstitute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kanazawa, Japan.

Chao WangInstitute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kanazawa, Japan.ORCID https://orcid.org/0000-0002-9165-7758

Shuto KosugeGraduate School of Pharmaceutical Sciences, Tohoku University, Sendai, Japan.

Yuji MatsuyaGraduate School of Medicine and Pharmaceutical Sciences, University of Toyama, Toyama, Japan.

Kenji SugimotoDepartment of Biomolecular Chemistry, Faculty of Science and Technology, Kyoto Prefectural University, Kyoto, Japan.ORCID https://orcid.org/0000-0003-3735-9343

Keiichi HiranoInstitute of Medical, Pharmaceutical, and Health Sciences, Kanazawa University, Kanazawa, Japan.ORCID https://orcid.org/0000-0002-2702-9183

Funding

Asahi Glass FoundationJSPS Grant-in-Aid for Scientific Research (B) 25K02385JSPS Grants-in-Aid for Grant-in-Aid for Challenging Research (Exploratory) 24K22017JST Fusion Oriented Research for Disruptive Science and Technology (FOREST) JPMJFR242BKobayashi FoundationSuzuken Memorial FoundationTakeda Science Foundation

6 · The paper itself

Abstract

Density Functional Theory (DFT) calculations were performed to elucidate the reaction mechanism of the Mg-catalyzed cyclization between an azadiene-type imine and a cyclopropane. The results reveal that the [4+3] cyclization pathway leading to azepine formation is both kinetically and thermodynamically preferred over the intuitively more accessible [3+2] pathway toward pyrrolidine formation. This unusual selectivity arises from the interplay of opposing electronic and steric effects, with steric effects ultimately dominating.

Indexed as

azepineDFT calculationLewis acidorthogonal relay catalysisreaction mechanism

Identifiers

PMID41934126

DOI10.1002/chem.70960

PMCPMC13282907

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