Effective synthesis of 3,5-diaryl-(1H)-pyrazin-2-ones via microwave mediated ring closure

被引：12
|
作者：
Johannes, Eugen [1 ]
Horbert, Rebecca [1 ]
Schlosser, Joachim [1 ,2 ]
Schmidt, Dorian [1 ]
Peifer, Christian [1 ]
机构：
[1] Univ Kiel, Inst Pharm, D-24118 Kiel, Germany
[2] Univ Tubingen, Inst Pharm, D-72076 Tubingen, Germany
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 31期
关键词：
3,5-Diaryl-(1H)-pyrazin-2-ones; Microwave reaction; Aryl-alpha-ketoamines; Aryl-glyoxylic acids; Protein kinase inhibitors; INHIBITORS; 2(1H)-PYRAZINONES; DESIGN; ALKALOIDS; SAR;
D O I：
10.1016/j.tetlet.2013.05.095
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
In this study we report on a flexible straight forward synthesis toward novel 3,5-diaryl-(1H)-pyrazin-2-ones. Our synthetic strategy involved an acyclic di-keto derivative as key intermediate. The final pyrazin-2-one ring closure reaction was yield-optimized by using a microwave mediated procedure and ammoniumacetate as nitrogen source. Our method is a suitable alternative to palladium-catalyzed coupling reactions for the 3,5-diaryl decoration of the (1H)-pyrazin-2-one scaffold. Since the (1H)-pyrazin-2-ones is present as scaffold in a number of biologically active compounds the reported synthetic platform is a useful approach to generate a set of highly diverse 3,5-diaryl-(1H)-pyrazin-2-one compounds. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4067 / 4072
页数：6
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