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Communication | Regular issue | Vol 45, No. 1, 1997, pp.1-5
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7618
Carbon-Carbon Bond Cleavage of α-Hydroxybenzylheteroarenes to Ketones and Heteroarenes by Catalytic Action of Cyanide Ion Based on Retro-Benzoin Condensation

Akira Miyashita,* Yumiko Suzuki, Yuki Takemura, Ken-ichi Iwamoto, and Takeo Higashino

*Schol of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan


Treatment of 4-(α-benzyl-α-hydroxybenzyl)quinazoline (2a) with potassium cyanide in DMF resulted in carbon-carbon bond cleavage to give benzyl phenyl ketone (3a) and quinazoline (4). Similar results were obtained with other 4-(α-hydroxybenzyl)quinalozines (2b-f and 7a). This reactioin proceeds through retrobenzoin condensation. This condensation also proceeded in pyrazolopyrimidine (9a) triazolopyrimidine (10a), quinoxaline (11a), and benzimidazole (12a), and the imidazolium salt (16) was an effective catalyst.