A NEW SYNTHETIC APPROACH TO THE C-D RING PORTION OF STREPTONIGRIN ANALOGS

被引：5

作者：

KILAMA, JJ ^{[1
]}

IYENGAR, BS ^{[1
]}

REMERS, WA ^{[1
]}

MASH, EA ^{[1
]}

机构：

[1] UNIV ARIZONA,DEPT CHEM,TUCSON,AZ 85721

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 05期

关键词：

D O I：

10.1002/jhet.5570270547

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Development of an efficient synthesis of the C‐D ring portion of streptonigrin is a key operation in the synthesis of this antibiotic and its analogues. A new method for the synthesis of 3‐cyano‐5,6‐dimethyl‐4‐(3,4,5‐trimethoxyphenyl)‐2‐pyridone (14), a compound having the requisite functionality for conversion into a streptonigrin analogue, has been established. It involves treatment of 3,4,5‐trimethoxybenzonitrile with ethylmagnesium bromide and malononitrile to give propylenemalononitrile derivative 7, which is condensed with trimethyl orthoacetate to give a mixture of 9 and pyridine derivative 12. Demethylation of 12 then affords 14. The overall yield for this route was 50%, allowing for conversion of 9 to 12. Copyright © 1990 Journal of Heterocyclic Chemistry

引用

页码：1437 / 1440

页数：4

共 14 条

[1] UTILIZATION OF BETA,GAMMA-UNSATURATED ALDEHYDE EQUIVALENTS IN SYNTHESIS OF SUBSTITUTED 2-HALONICOTINIC ACID-DERIVATIVES [J].