3 years ago

One-Pot Synthetic Approaches for the Construction of Isochroman-4-ones and Benzoxazin-3-ones Using O,P-Acetals

Tomohiro Maegawa, Akira Nakamura, Kouhei Yamamoto, Ryo Murakami, Norihito Kawashita, Kouichi Matsumoto

A method for synthesizing six-membered heterocyclic compounds was developed based on the features of O,P-acetals. Sequential reactions of intramolecular cyclization between the methylene carbon atom of O,P-acetal and its electrophilic functional group (ester or protected carbamate) was followed by Horner–Wadsworth–Emmons (HWE) olefination with various aldehydes. The developed one-pot method yielded isochroman-4-one and benzoxazin-3-one derivatives with an alkylidene moiety. Received: 06 May 2021

Accepted after revision: 04 June 2021

Publication Date:
04 June 2021 (online) © 2021. Thieme. All rights reserved Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

Publisher URL: http://dx.doi.org/10.1055/a-1523-1597

DOI: 10.1055/a-1523-1597

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