Cyclization Reactions of 1,2-Bis(2-cyanophenyl)propionitriles. I. Structure of the "Red Pigment" formed by the Base-catalyzed Cyclization of 1,2-Bis(2-cyano-3-methoxyphenyl)propionitrile in the Presence of Diethyl Carbonate
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概要
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The reaction of 1,2-bis(2-cyano-3-methoxyphenyl)propionitrile (<B>1</B>) with diethyl carbonate and sodium ethoxide gave a red pigment <B>2</B>, C<SUB>22</SUB>H<SUB>19</SUB>N<SUB>3</SUB>O<SUB>4</SUB> in 79% yield. It afforded 5-amino-4,7-dimethoxy-11<I>H</I>-indeno[1,2-<I>c</I>]isoquinolin-11-one (<B>4</B>) on treatment with alkaline hydrogen peroxide. The "red pigment" has been confirmed to have a novel 5<I>H</I>-indeno[1,2-<I>c</I>]isoquinoline structure which transforms into colorless 11<I>H</I>-indeno-[1,2-<I>c</I>]isoquinoline form in an acidic medium. The mechanism of the formation of <B>2</B> from <B>1</B> imparts an interesting problem as regards carbanion reactivity.
- 公益社団法人 日本化学会の論文
著者
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Kubota Takashi
Faculty Of Medicine Kinki University
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Ando Kazuo
Faculty of Science, Osaka City University
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Yama Takashi
Faculty of Science, Osaka City University
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