Carbon-Carbon Bond Cleavage of α-Hydroxybenzylheteroarenes Catalyzed by Cyanide Ion : Retro-Benzoin Condensation Affords Ketones and Heteroarenes and Benzyl Migration Affords Benzylheteroarenes and Arenecarbaldehydes
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概要
- 論文の詳細を見る
4-(α-Benzyl-α-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4,9,12,16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford ketones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13,14,15) having an α-benzyl-α-hydroxybenzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11,Bu_4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4-aroylquinazolines (34), using the aroyl group as a protecting and electron-withdrawing group.
- 公益社団法人日本薬学会の論文
- 1998-02-15
著者
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Suzuki Y
School Of Pharmaceutical Sciences University Of Shizuoka
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Suzuki Y
Fukuoka Inst. Technol. Fukuoka
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Suzuki Y
Department Of Pharmacobiology And Therapeutics Faculty Of Pharmacy Meijo University
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Suzuki Y
Core Research For Evolutional Science And Technology (crest Jst) University Of Shizuoka School Of Ph
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MIYASHITA Akira
School of Pharmaceutical Sciences, University of Shizuoka
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SUZUKI Yumiko
School of Pharmaceutical Sciences, University of Shizuoka
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IWAMOTO Ken-ichi
School of Pharmaceutical Sciences, University of Shizuoka
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HIGASHINO Takeo
School of Pharmaceutical Sciences, University of Shizuoka
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TAKEMURA Yuki
School of Pharmaceutical Sciences, University of Shizuoka
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Suzuki Yumiko
School Of Pharmaceutical Sciences University Of Shizuoka
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Takemura Y
Faculty Of Pharmaceutical Sciences Mukogawa Women's University
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Takemura Yuki
School Of Pharmaceutical Sciences University Of Shizuoka
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Iwamoto K
Eisai Co. Ltd. Gifu Jpn
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Miyashita A
School Of Pharmaceutical Sciences University Of Shizuoka
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Miyashita A
Department Of Applied Chemistry Faculty Of Engineering Saitama University
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Miyashita Akira
Department Of Applied Physics School Of Engineering Nagoya University
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Miyashita Akira
School Of Pharmaceutical Sciences University Of Shizuoka
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Higashino Tt
School Of Pharmaceutical Sciences University Of Shizuoka
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Suzuki Yumiko
School Of Pharmaceutical Sciences Toho University
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Iwamoto Ken-ichi
School Of Pharmaceutical Sciences University Of Shizuoka
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