SYNTHESIS OF 2-SUBSTITUTED 2,3-DIHYDRO-9-PHENYL-1H-PYRROLO[3,4-B]QUINOLIN-3-ONES AS POTENTIAL PERIPHERAL BENZODIAZEPINE-RECEPTOR LIGANDS

被引：0
|
作者：
ANZINI, M
CAPPELLI, A
VOMERO, S
机构：
来源：
HETEROCYCLES | 1994年 / 38卷 / 01期
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D O I：
暂无
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Two synthetic routes to the achievement of the title compounds are described. 2-Chloromethyl-3-ethoxycarbonyl-4-phenylquinoline (4) was transfomed into the corresponding lacton (5) which in two steps was converted into its isomeric lacton (7). Aminolysis of 7 gave gamma-hydroxyamide (8) which was in turn transformed into gamma-chloroamide (9). Cyclization of 9 with sodium hydride in presence of oxygen led to the oxidized compound (10), while by carrying out the cyclization reaction under inert atmosphere, 2-benzyl-2,3-dihydro-9-phenyl-1H-pyrrolo[3,4-b]quinolin-3-one (3a) was obtained. Autoxidation of anion at 1-position of compound (3a) was considered to account for these results and a mechanistical interpretation was given. A simplier and more versatile route to obtain the title compounds was also developed.
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页码：103 / 111
页数：9
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