Carbon-Carbon Bond Cleavage of. ALPHA.-Hydroxybenzylheteroarenes Catalyzed by Cyanide Ion: Retro-Benzoin Condensation Affords Ketones and Heteroarenes …

…, K Iwamoto, T HIGASHINO, AK MIYASHITA

Index: Suzuki, Yumiko; Takemura, Yuki; Iwamoto, Ken-Ichi; Higashino, Takeo; Miyashita, Akira Chemical and Pharmaceutical Bulletin, 1998 , vol. 46, # 2 p. 199 - 206

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Citation Number: 22

Abstract

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 ...