Efficient and Practical Synthesis of β-Naphthol-Substituted 2-Azetines via Vinylidene ortho-Quinone Methide (VQM) Intermediates.

Authors

Aoto Suzuki, Ryo Hirokawa, Hayate Takeuchi, Kenji Yamashita, Yoshitaka Hamashima

Published in

Chemical & pharmaceutical bulletin. Volume 74. Issue 10. Pages 742-746.

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.

PMID:
42816360
Bibliographic data and abstract were imported from PubMed on 01 Oct 2026.

Read full publication at:
Please sign in to see all details.

Stats

1-terrible, 9-excellent. How would you rate this publication? Sign in in to submit your rating.

Post a comment

You need to be signed in to post comments. You can sign in here.

Comments

There are no comments yet.