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NITROGEN BRIDGEHEAD COMPOUNDS .80. UNUSUAL REACTION OF ETHYL 9-BROMO-4-OXO-6,7,8,9-TETRAHYDRO-4H-PYRIDO[1,2-A]PYRIMIDINE-3-CARBOXYLATES AND N-METHYLANILINE

被引：3
|
作者：
HERMECZ, I
BREINING, T
SIMON, K
EROSTAKACSY, T
PODANYI, B
SESSI, J
机构：
[1] CHINOIN Pharmaceutical and Chemical Works Ltd., Budapest, H-1325
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1991年 / 28卷 / 05期
关键词：
D O I：
10.1002/jhet.5570280536
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The acid-catalysed intramolecular nucleophilic addition of the phenyl ring to the C(9a) = N(1) double bond of ethyl 9-(N-methyl-N-phenyl)-4-oxotetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylates, formed in the reactions of ethyl 9-bromo-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidine-3-carboxylates and N-methylaniline, gave the first examples of a new tetracyclic pyrimido[l',2':1,2]pyrido[3,2-b]indole ring system (7). X-ray diffraction analysis of 7a revealed that the annelation of the pyrimidine and piperidine rings is transoid, while that of the piperidine and pyrroline rings is cis, the piperidine ring adopts an unusual 6T8 twisted boat conformation, while the pyrroline ring has a 9T8a conformation.
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收藏
页码：1405 / 1411
页数：7
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