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Synthesis 2021; 53(20): 3862-3868
DOI: 10.1055/a-1523-1597
paper

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

Akira Nakamura 
a   School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
,
Kouhei Yamamoto
a   School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
,
Ryo Murakami
a   School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
,
Norihito Kawashita 
b   Department of Life Science, School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
,
Kouichi Matsumoto
c   Department of Chemistry, School of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
,
Tomohiro Maegawa  ∗
a   School of Pharmaceutical Sciences, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan
› Author AffiliationsThis work was financially supported by JSPS KAKENHI Grant Numbers 19K16329 and 18K05132, and also supported by 2021 Kindai University Research Enchancement Grant (KD2106).
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Abstract

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.

Key words

isochroman-4-one - benzoxazin-3-one - Horner–Wadsworth–Emmons reaction - organophosphorus compound

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1523-1597.
  • Supporting Information


Publication History

Received: 06 May 2021

Accepted after revision: 04 June 2021

Accepted Manuscript online:
04 June 2021

Article published online:
29 June 2021

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