Trapped Cycloadducts of 1-Azabutadienes via Microwave-Assisted Ring Opening of N-Acyl-2-azetines
Su C, Cameron JP, Bernhardt PV, Clark T, Williams CM (2026)
Publication Type: Journal article
Publication year: 2026
Journal
Book Volume: 91
Pages Range: 8144-8150
Journal Issue: 24
Abstract
Disclosed herein is the observation that electrocyclic ring opening of select N-acyl-2-azetines can occur under microwave irradiation or conventional heating to give the corresponding 1-azabutadiene systems, under more mild and accessible conditions than the previously reported flash vacuum pyrolysis conditions. The intermediate 1-azabutadienes, successfully detected by NMR analysis in the case of the 2-naphthoyl system, subsequently undergo intermolecular Diels–Alder reactions with the parent azetine systems to form heterobicyclic dimers, as confirmed by X-ray crystallography. Alternatively, if the 1-azabutadiene is generated in the presence of an electron-rich dienophile (e.g., enol ether or enamine), dimer formation is partially or fully suppressed, giving the corresponding cycloadducts instead. These observations are in agreement with the included theoretical calculations.
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APA:
Su, C., Cameron, J.P., Bernhardt, P.V., Clark, T., & Williams, C.M. (2026). Trapped Cycloadducts of 1-Azabutadienes via Microwave-Assisted Ring Opening of N-Acyl-2-azetines. Journal of Organic Chemistry, 91(24), 8144-8150. https://doi.org/10.1021/acs.joc.6c00244
MLA:
Su, Chuyi, et al. "Trapped Cycloadducts of 1-Azabutadienes via Microwave-Assisted Ring Opening of N-Acyl-2-azetines." Journal of Organic Chemistry 91.24 (2026): 8144-8150.
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