Peer-reviewedCC BY-NCChemical and Pharmaceutical Bulletin
Efficient and Practical Synthesis of β-Naphthol-Substituted 2-Azetines via Vinylidene ortho-Quinone Methide (VQM) Intermediates
Abstract
We report an efficient and practical strategy for the synthesis of bromo-substituted 2-azetines bearing a β-naphthol moiety. The reaction proceeds via the formation of highly reactive vinylidene ortho-quinone methide (VQM) intermediates, followed by intramolecular bromocyclization to afford highly strained 2-azetines under mild conditions. Notably, the cyclization step is significantly facilitated by catalytic Schreiner's urea. This protocol is readily scalable, and the strategically incorporated bromo group in the product provides a convenient handle for further derivatization.
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BibTeX
@article{suzuki2026efficient,
title = {{Efficient and Practical Synthesis of β-Naphthol-Substituted 2-Azetines via Vinylidene ortho-Quinone Methide (VQM) Intermediates}},
author = {Aoto Suzuki and Ryo Hirokawa and Hayate Takeuchi and Kenji Yamashita and Yoshitaka Hamashima},
journal = {Chemical and Pharmaceutical Bulletin},
year = {2026},
month = oct,
doi = {10.1248/cpb.c26-00411},
url = {https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00411/_article},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - Efficient and Practical Synthesis of β-Naphthol-Substituted 2-Azetines via Vinylidene ortho-Quinone Methide (VQM) Intermediates
AU - Aoto Suzuki
AU - Ryo Hirokawa
AU - Hayate Takeuchi
AU - Kenji Yamashita
AU - Yoshitaka Hamashima
PY - 2026
DA - 2026/10/01
JO - Chemical and Pharmaceutical Bulletin
DO - 10.1248/cpb.c26-00411
UR - https://www.jstage.jst.go.jp/article/cpb/74/10/74_c26-00411/_article
AB - We report an efficient and practical strategy for the synthesis of bromo-substituted 2-azetines bearing a β-naphthol moiety. The reaction proceeds via the formation of highly reactive vinylidene ortho-quinone methide (VQM) intermediates, followed by intramolecular bromocyclization to afford highly strained 2-azetines under mild conditions. Notably, the cyclization step is significantly facilitated by catalytic Schreiner's urea. This protocol is readily scalable, and the strategically incorporated bromo group in the product provides a convenient handle for further derivatization.
SN - 1347-5223
SN - 0009-2363
ER -