A NOVEL SYNTHETIC ROUTE TO 1,2-DIMETHYL-5-PHENYL-1H-IMIDAZO[4,5-B]PYRIDIN-7-OL

被引:1
|
作者
LIS, R [1 ]
TRAINA, JA [1 ]
HUFFMAN, JC [1 ]
机构
[1] INDIANA UNIV,CTR MOLEC STRUCT,BLOOMINGTON,IN 47405
关键词
D O I
10.1002/jhet.5570270311
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Heating a mixture of 4‐amino‐1,2‐dimethyl‐1H‐imidazole‐5‐carboxylic acid ethyl ester with ethyl benzoyl acetate resulted in the formation of 8‐ethoxycarbonyl‐6,7‐dimethyl‐4‐oxo‐2‐phenylimidazo[1,5‐a]pyrimidin‐5‐ium, hydroxide, inner salt. This compound was then transformed into 1,2‐dimethyl‐5‐phenyl‐1H‐imidazo‐[4,5‐b]pyridin‐7‐ol via several intermediates. A number of structurally interesting compounds were also isolated during the course of this work. Thus, the target ring system was formed by a circuitous series of ring‐chain tautomerizations/rearrangements. Copyright © 1990 Journal of Heterocyclic Chemistry
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页码:531 / 534
页数:4
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