Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones
Comparative study of synthetic approaches to 1-arylmethylenepyrazino[2,1-b]quinazoline-3,6-diones
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DOI：
10.1016/s0040-4020(98)00744-3
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发表时间：
1998-10-01
期刊：
影响因子：
2.1
通讯作者：
Menéndez, JC
中科院分区：
文献类型：
--
作者：
Cledera, P;Avendaño, C;Menéndez, JC
研究了3-芳基亚甲基哌嗪-2,5-二酮(1)转化为1-芳基亚甲基-2,4-二氢-1H-吡嗪基[2,1-b]喹唑啉-3,6-二酮(2)。比较了四种合成方法，即邻氨基苯甲酸与亚硫酰氯反应产物直接缩合、转化为单硫代亚氨基醚或单亚氨基醚再与邻氨基苯甲酸衍生物反应、邻叠氮基苯甲酰氯单酰化再进行分子内氮杂维蒂希反应。后一种方法获得了最好的结果。 (C) 1998 Elsevier Science Ltd. 保留所有权利。
The transformation of 3-arylmethylenepiperazine-2,5-diones (1) into 1-arylmethylene-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones (2) was studied. Four synthetic methods were compared, namely direct condensation with the product of the reaction between anthranilic acid and thionyl chloride, transformation into monothioiminoethers or monoiminoethers followed by reaction with anthranilic acid derivatives, and monoacylation with o-azidobenzoyl chloride followed by intramolecular aza-Wittig reaction. The best results were obtained by the latter method. (C) 1998 Elsevier Science Ltd. All rights reserved.