Reactions ofo‐aminonitriles with isocyanates. 2. A facile synthesis of imidazo[1,2‐c]quinazoline‐2,5‐(3H,6H)dione
作者:
Eleftherios Paul Papadopoulos,
期刊:
Journal of Heterocyclic Chemistry
(WILEY Available online 1981)
卷期:
Volume 18,
issue 3
页码: 515-518
ISSN:0022-152X
年代: 1981
DOI:10.1002/jhet.5570180315
出版商: Wiley‐Blackwell
数据来源: WILEY
摘要:
AbstractAnthranilonitrile reacts with ethyl isocyanatoacetate to form 2‐(3‐ethoxycarbonylmethylureido)benzonitrile (3b) which, upon heating, or treatment with a base, undergoes a double cyclization to yield imidazo[1,2‐c]‐quinazoline‐2,5‐(3H,6H)dione (5) in excellent yield. In the presence of acid,3bis converted into 1,4‐dihydro‐2,4‐dioxo‐3‐(2H)quinazolineacetic acid (11), or its ethyl ester (10). The action of concentrated sulfuric acid converts the adduct13of anthranilic acid and ethyl isocyanatoacetate into 2‐ethoxycarbonyl‐methylamino‐4H
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