Alkylation of the sulfur- and nitrogen-containing compounds analogous to thiazoline systems.
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概要
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<I>N</I>,<I>N</I>-Dimethyl-2-(alkylthio)ethylamines and 3-methylthiazolidines underwent <I>N</I>-methylation both with trimethyloxonium tetrafluoroborate (<B>3a</B>) and with methyl iodide. In the methylation of <I>N</I>,<I>N</I>-dimethyl-<I>o</I>-(methylthio)aniline, the main reaction was <I>S</I>-methylation. On the other hand, in the <I>o</I>-ethylthio derivative, <I>S</I>-methylated product was major with methyl iodide, while <I>N</I>-methylated product was major with <B>3a</B>. In the <I>N</I>-ethyl or <I>N</I>-benzyl derivative, only <I>S</I>-methylation occurred with both reagents. 3-Methyl-2, 2-diphenyl-2,3-dihydro-benzothiazole gave <I>S</I>-methylated product with <B>3a</B>, suggesting that <I>S</I>-methylation becomes major when the 2-substituent is bulkier. 4-Methyl-3,4-dmydro-2<I>H</I>-benzo[<I>b</I>][1,4]thiazine was methylated on the nitrogen with <B>3a</B>, while it gave <I>S</I>-methylated product with methyl iodide. Phenothiazines and 1-dialkylamino-8-(methylthio)naphthalenes gave only <I>S</I>-methylated products. The selective <I>S</I>-methylation in the case of <I>N</I>-methylation was carried out through protonation on the nitrogen atom followed by methylation with <B>3a</B>. Possibility of intramolecular interaction between sulfonio and amino groups has been discussed based on their NMR data.
- 公益社団法人 日本化学会の論文
著者
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Akiba Kin-ya
Department Of Chemistry Faculty Of Science Hiroshima University
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Inamoto Naoki
Department Of Chemistry Graduate School Of Science The University Of Tokyo
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Ohara Yoshio
Department of Chemistry, Faculty of Science, The University of Tokyo
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