Synthesis of 1H-2-Benzopyran-5,8-dione Skeleton through a Cascade Reaction between Benzoquinone and β-Ketoester

Masataka Nakahara; Hiroyoshi Ohtsu; Masaki Kawano; Kengo Hanaya; Takeshi Sugai; Shuhei Higashibayashi

doi:10.1246/cl.210817

Synthesis of 1H-2-Benzopyran-5,8-dione Skeleton through a Cascade Reaction between Benzoquinone and β-Ketoester

Masataka Nakahara, Hiroyoshi Ohtsu, Masaki Kawano, Kengo Hanaya, Takeshi Sugai, Shuhei Higashibayashi

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

The 1H-2-benzopyran-5,8-dione structure was synthesized by a cascade reaction through Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters under basic conditions. The reaction using potassium carbonate and 18-crown-6 in THF was the best condition, giving 1H-2-benzopyran-5,8-dione derivatives in good yields. The UV-vis absorption spectrum and cyclic voltammogram of the synthesized 1H-2-benzopyran-5,8-dione derivative were measured, clarifying the photophysical and redox properties.

Original language	English
Pages (from-to)	356-359
Number of pages	4
Journal	Chemistry Letters
Volume	51
Issue number	4
DOIs	https://doi.org/10.1246/cl.210817
Publication status	Published - 2022 Apr

Keywords

1H-2-Benzopyran-5,8-dione
Cascade reaction
Physical property

ASJC Scopus subject areas

Chemistry(all)

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10.1246/cl.210817

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title = "Synthesis of 1H-2-Benzopyran-5,8-dione Skeleton through a Cascade Reaction between Benzoquinone and β-Ketoester",

abstract = "The 1H-2-benzopyran-5,8-dione structure was synthesized by a cascade reaction through Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters under basic conditions. The reaction using potassium carbonate and 18-crown-6 in THF was the best condition, giving 1H-2-benzopyran-5,8-dione derivatives in good yields. The UV-vis absorption spectrum and cyclic voltammogram of the synthesized 1H-2-benzopyran-5,8-dione derivative were measured, clarifying the photophysical and redox properties.",

keywords = "1H-2-Benzopyran-5,8-dione, Cascade reaction, Physical property",

author = "Masataka Nakahara and Hiroyoshi Ohtsu and Masaki Kawano and Kengo Hanaya and Takeshi Sugai and Shuhei Higashibayashi",

note = "Funding Information: This work was supported by JSPS KAKENHI Grant Number JP20K05499 (S.H.), JP20H04662 (M.K.), and Fukuoka Naohiko Memorial Foundation (S.H.). The X-ray crystallographic analysis was performed under the approval of the Photon Factory Program Advisory Committee (Proposal No. 2021G046). The computations were performed at the Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: {\textcopyright} 2022 The Chemical Society of Japan",

year = "2022",

month = apr,

doi = "10.1246/cl.210817",

language = "English",

volume = "51",

pages = "356--359",

journal = "Chemistry Letters",

issn = "0366-7022",

publisher = "Chemical Society of Japan",

number = "4",

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TY - JOUR

T1 - Synthesis of 1H-2-Benzopyran-5,8-dione Skeleton through a Cascade Reaction between Benzoquinone and β-Ketoester

AU - Nakahara, Masataka

AU - Ohtsu, Hiroyoshi

AU - Kawano, Masaki

AU - Hanaya, Kengo

AU - Sugai, Takeshi

AU - Higashibayashi, Shuhei

N1 - Funding Information: This work was supported by JSPS KAKENHI Grant Number JP20K05499 (S.H.), JP20H04662 (M.K.), and Fukuoka Naohiko Memorial Foundation (S.H.). The X-ray crystallographic analysis was performed under the approval of the Photon Factory Program Advisory Committee (Proposal No. 2021G046). The computations were performed at the Research Center for Computational Science, Okazaki, Japan. Publisher Copyright: © 2022 The Chemical Society of Japan

PY - 2022/4

Y1 - 2022/4

N2 - The 1H-2-benzopyran-5,8-dione structure was synthesized by a cascade reaction through Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters under basic conditions. The reaction using potassium carbonate and 18-crown-6 in THF was the best condition, giving 1H-2-benzopyran-5,8-dione derivatives in good yields. The UV-vis absorption spectrum and cyclic voltammogram of the synthesized 1H-2-benzopyran-5,8-dione derivative were measured, clarifying the photophysical and redox properties.

AB - The 1H-2-benzopyran-5,8-dione structure was synthesized by a cascade reaction through Michael addition, elimination of HBr, and O-alkylation between a dibromobenzoquinone derivative and β-ketoesters under basic conditions. The reaction using potassium carbonate and 18-crown-6 in THF was the best condition, giving 1H-2-benzopyran-5,8-dione derivatives in good yields. The UV-vis absorption spectrum and cyclic voltammogram of the synthesized 1H-2-benzopyran-5,8-dione derivative were measured, clarifying the photophysical and redox properties.

KW - 1H-2-Benzopyran-5,8-dione

KW - Cascade reaction

KW - Physical property

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DO - 10.1246/cl.210817

M3 - Article

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SN - 0366-7022

VL - 51

SP - 356

EP - 359

JO - Chemistry Letters

JF - Chemistry Letters

IS - 4

ER -

Synthesis of 1H-2-Benzopyran-5,8-dione Skeleton through a Cascade Reaction between Benzoquinone and β-Ketoester

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Keywords

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