Reaction of Benzoxazoline-2-thiones with Alkyl Halides

Masatoshi Yamato; Yasuo Takeuchi; Kuniko Hashigaki; Takashi Hirota

doi:10.1248/cpb.31.733

Reaction of Benzoxazoline-2-thiones with Alkyl Halides

Masatoshi Yamato, Yasuo Takeuchi, Kuniko Hashigaki, Takashi Hirota

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

6 Citations (Scopus)

Abstract

The effect of the solvent on the reaction of benzoxazoline-2-thiones with alkyl halides was studied. The reaction of 1 with alkyl halides and potassium carbonate in dimethylformamide (DMF) gave the corresponding 2-alkylthiobenzoxazoles (2), but the same reaction gave 2-methoxybenzoxazoles (4a) when methanol was used in place of DMF as the solvent. On the other hand, the reaction of 1, methyl iodide, alcohol, and sodium hydride in tetrahydrofuran (THF) gave 2-[N-(dialkoxymethylene)amino]phenols (5).

Original language	English
Pages (from-to)	733-736
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	31
Issue number	2
DOIs	https://doi.org/10.1248/cpb.31.733
Publication status	Published - 1983

Keywords

2-[N-(dialkoxy-methylene)amino]phenol
2-alkoxybenzoxazole
alkylation
benzoxazoline-2-thione
solvent effect

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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title = "Reaction of Benzoxazoline-2-thiones with Alkyl Halides",

abstract = "The effect of the solvent on the reaction of benzoxazoline-2-thiones with alkyl halides was studied. The reaction of 1 with alkyl halides and potassium carbonate in dimethylformamide (DMF) gave the corresponding 2-alkylthiobenzoxazoles (2), but the same reaction gave 2-methoxybenzoxazoles (4a) when methanol was used in place of DMF as the solvent. On the other hand, the reaction of 1, methyl iodide, alcohol, and sodium hydride in tetrahydrofuran (THF) gave 2-[N-(dialkoxymethylene)amino]phenols (5).",

keywords = "2-[N-(dialkoxy-methylene)amino]phenol, 2-alkoxybenzoxazole, alkylation, benzoxazoline-2-thione, solvent effect",

author = "Masatoshi Yamato and Yasuo Takeuchi and Kuniko Hashigaki and Takashi Hirota",

year = "1983",

doi = "10.1248/cpb.31.733",

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T1 - Reaction of Benzoxazoline-2-thiones with Alkyl Halides

AU - Yamato, Masatoshi

AU - Takeuchi, Yasuo

AU - Hashigaki, Kuniko

AU - Hirota, Takashi

PY - 1983

Y1 - 1983

N2 - The effect of the solvent on the reaction of benzoxazoline-2-thiones with alkyl halides was studied. The reaction of 1 with alkyl halides and potassium carbonate in dimethylformamide (DMF) gave the corresponding 2-alkylthiobenzoxazoles (2), but the same reaction gave 2-methoxybenzoxazoles (4a) when methanol was used in place of DMF as the solvent. On the other hand, the reaction of 1, methyl iodide, alcohol, and sodium hydride in tetrahydrofuran (THF) gave 2-[N-(dialkoxymethylene)amino]phenols (5).

AB - The effect of the solvent on the reaction of benzoxazoline-2-thiones with alkyl halides was studied. The reaction of 1 with alkyl halides and potassium carbonate in dimethylformamide (DMF) gave the corresponding 2-alkylthiobenzoxazoles (2), but the same reaction gave 2-methoxybenzoxazoles (4a) when methanol was used in place of DMF as the solvent. On the other hand, the reaction of 1, methyl iodide, alcohol, and sodium hydride in tetrahydrofuran (THF) gave 2-[N-(dialkoxymethylene)amino]phenols (5).

KW - 2-[N-(dialkoxy-methylene)amino]phenol

KW - 2-alkoxybenzoxazole

KW - alkylation

KW - benzoxazoline-2-thione

KW - solvent effect

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Reaction of Benzoxazoline-2-thiones with Alkyl Halides

Abstract

Keywords

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