A New Method for the Preparation of 2-Alkoxybenzoxazoles

Masatoshi Yamato; Yasuo Takeuchi; Kyoko Hattori; Kuniko Hashigaki

doi:10.1248/cpb.31.3946

A New Method for the Preparation of 2-Alkoxybenzoxazoles

Masatoshi Yamato, Yasuo Takeuchi, Kyoko Hattori, Kuniko Hashigaki

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

2 Citations (Scopus)

Abstract

A one-pot synthesis of 2-alkoxybenzoxazole (I) from benzoxazoline-2-thione (II) was achieved. Treatment of benzoxazoline-2-thione with methyl iodide followed by an alcohol at room temperature in the presence of sodium hydride gave I. The reaction involves the intermediate of 2-(methylthio)benzoxazole (IIIa), followed by substitution of the methylthio group by an alkoxide anion. The general applicability of this method is discussed.

Original language	English
Pages (from-to)	3946-3950
Number of pages	5
Journal	Chemical and Pharmaceutical Bulletin
Volume	31
Issue number	11
DOIs	https://doi.org/10.1248/cpb.31.3946
Publication status	Published - Aug 1983

Keywords

2-(alkylthio)benzoxazole
2-(dialkoxymethylene)aminophenol
2-alkoxybenzoxazole
4-tert-butylcyclohexanol
benzoxazoline-2-thione

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.31.3946

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title = "A New Method for the Preparation of 2-Alkoxybenzoxazoles",

abstract = "A one-pot synthesis of 2-alkoxybenzoxazole (I) from benzoxazoline-2-thione (II) was achieved. Treatment of benzoxazoline-2-thione with methyl iodide followed by an alcohol at room temperature in the presence of sodium hydride gave I. The reaction involves the intermediate of 2-(methylthio)benzoxazole (IIIa), followed by substitution of the methylthio group by an alkoxide anion. The general applicability of this method is discussed.",

keywords = "2-(alkylthio)benzoxazole, 2-(dialkoxymethylene)aminophenol, 2-alkoxybenzoxazole, 4-tert-butylcyclohexanol, benzoxazoline-2-thione",

author = "Masatoshi Yamato and Yasuo Takeuchi and Kyoko Hattori and Kuniko Hashigaki",

year = "1983",

month = aug,

doi = "10.1248/cpb.31.3946",

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pages = "3946--3950",

journal = "Chemical and Pharmaceutical Bulletin",

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T1 - A New Method for the Preparation of 2-Alkoxybenzoxazoles

AU - Yamato, Masatoshi

AU - Takeuchi, Yasuo

AU - Hattori, Kyoko

AU - Hashigaki, Kuniko

PY - 1983/8

Y1 - 1983/8

N2 - A one-pot synthesis of 2-alkoxybenzoxazole (I) from benzoxazoline-2-thione (II) was achieved. Treatment of benzoxazoline-2-thione with methyl iodide followed by an alcohol at room temperature in the presence of sodium hydride gave I. The reaction involves the intermediate of 2-(methylthio)benzoxazole (IIIa), followed by substitution of the methylthio group by an alkoxide anion. The general applicability of this method is discussed.

AB - A one-pot synthesis of 2-alkoxybenzoxazole (I) from benzoxazoline-2-thione (II) was achieved. Treatment of benzoxazoline-2-thione with methyl iodide followed by an alcohol at room temperature in the presence of sodium hydride gave I. The reaction involves the intermediate of 2-(methylthio)benzoxazole (IIIa), followed by substitution of the methylthio group by an alkoxide anion. The general applicability of this method is discussed.

KW - 2-(alkylthio)benzoxazole

KW - 2-(dialkoxymethylene)aminophenol

KW - 2-alkoxybenzoxazole

KW - 4-tert-butylcyclohexanol

KW - benzoxazoline-2-thione

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DO - 10.1248/cpb.31.3946

M3 - Article

AN - SCOPUS:0021012995

SN - 0009-2363

VL - 31

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EP - 3950

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 11

ER -

A New Method for the Preparation of 2-Alkoxybenzoxazoles

Abstract

Keywords

ASJC Scopus subject areas

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