Synthesis and tautomerism of 1,5-bis(alkylamino)-4H-benzo(a)phenothiazin-4-ones.
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概要
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The equimolecular condensation of 2-aminobenzenethiol (<B>1</B>) with 4,8-bis(alkylamino)-1,5-naphthoquinones (<B>2</B>) in ethanol in the presence of HCl gave near-infrared-absorbing 1,5-bis(alkylamino)-4<I>H</I>-benzo[<I>a</I>]phenothiazin-4-ones (<B>3</B>), which existed as predominant tautomers in various solvents. The reaction mechanism was proposed to involve pathways through the <I>O</I>-protonation of <B>2</B>, followed by the attack of <B>1</B> on the resulting ion, the subsequent oxidation, and the acid-catalyzed intramolecular cyclization of the quinonoid intermediate. The tautomeric equilibria of <B>2</B>, <B>3</B>, and 5,8-dihydroxy-1,4-naphthoquinone favor the formation of an interconverting hydrogen atom of a higher electron density. The solvatochromic effect of <B>3</B> was analyzed by means of the linear solvation energy relationships.
- 公益社団法人 日本化学会の論文
著者
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Ishida Tetsuya
Department Of Anatomy Kagawa Medical University
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Ueno Yoshio
Department Of Applied Chemistry Nagoya Institute Of Technology
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Hasegawa Kan-ichi
Department of Natural Science, Nagoya University of Arts
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Sakakibara Makoto
Department of Applied Chemistry, Nagoya Institute of Technology
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