SYNTHESIS OF 7-AMINO-1,4-DIHYDRO-4-OXO-6-(TRIFLUOROMETHYL)-1,8-NAPHTHYRIDINES - THE USE OF METHYLIDENEMALONATE AS AN ACTIVATING GROUP AND A SULFUR ASSISTED CYCLIZATION

被引:8
作者
BRIDGES, AJ
SANCHEZ, JP
机构
[1] Department of Chemistry, Parke-Davis Pharmaceutical Research Division, Warner-Lambert Company, Ann Arbor, Michigan, 48105
[2] Eisai Research Institute, Andover, Massachusetts, 01810
关键词
D O I
10.1002/jhet.5570270602
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2,6‐Dichloro‐3‐(trifluoromethyl)pyridine 3 was used to develop a six‐step preparation of 7‐amino‐4‐oxo‐6‐(trifluoromethyl)naphthyridines. The CF3 group deactivated the pyridine ring towards both nucleophiles and electrophiles. A new reagent for pyridone annulation, the aminomethylidenemalonate anion, is described, along with several strategies to manipulate the electron density of substituted pyridines. Copyright © 1990 Journal of Heterocyclic Chemistry
引用
收藏
页码:1527 / 1536
页数:10
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