Carbon-carbon bond cleavage of alpha-hydroxybenzylheteroarenes to ketones and heteroarenes by catalytic action of cyanide ion based on retrobenzoin condensation

被引：2
|
作者：
Miyashita, A
Suzuki, Y
Takemura, Y
Iwamoto, K
Higashino, T
机构：
[1] School of Pharmaceutical Sciences, University of Shizuoka, Shizuoka 422
来源：
HETEROCYCLES | 1997年 / 45卷 / 01期
关键词：
D O I：
10.3987/COM-96-7618
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Treatment of 4-(alpha-benzyl-alpha-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-(alpha-hydroxybenzyl)quinazolines (2b-f and 7a). This reaction 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.
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页码：1 / 5
页数：5
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