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New tetrasubstituted isonicotinic acid derivatives based on malononitrile. Reactions of sodium 2,6-diamino-3,5-dicyanopyridine-4-carboxylate
Russian Journal of Organic Chemistry ( IF 0.8 ) Pub Date : 2016-09-01 , DOI: 10.1134/s1070428016090244
A. M. Khil’ , N. Yu. Garmash , V. A. Kaminskii

Due to the presence of several reactive cyano groups polycyano compounds are used as starting materials for the synthesis of various heterocycles. High synthetic potential of these compounds allows preparation of various structures containing furan [1], pyrrole [2], or pyridine [3] fragments. Promising polycyano compounds are salts 1 derived from prop-1-ene1,1,2,3,3-pentacarbonitrile. These salts have become readily accessible after development of a new method for their preparation via reaction of malononitrile with selenium dioxide in the presence of bases [4]. Alkaline hydrolysis of 1 is accompanied by heterocyclization to pyrrolidinone derivatives which then undergo recyclization to 2,6-diamino-3,5-dicyanopyridine-4-carboxylic acid salts [5]. Some isonicotinic acid derivatives exhibit biological activity; examples are isoniazid and derivatives of 3-carbamoyl-, 2-amino-, and 2,5-diaminoisonicotinic acids which show antibacterial ISSN 1070-4280, Russian Journal of Organic Chemistry, 2016, Vol. 52, No. 9, pp. 1370–1373. © Pleiades Publishing, Ltd., 2016. Original Russian Text © A.M. Khil’, N.Yu. Garmash, V.A. Kaminskii, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1378–1381.

中文翻译:

基于丙二腈的新型四取代异烟酸衍生物。2,6-二氨基-3,5-二氰基吡啶-4-羧酸钠的反应

由于存在几个反应性氰基,多氰基化合物被用作合成各种杂环的原料。这些化合物的高合成潜力允许制备包含呋喃 [1]、吡咯 [2] 或吡啶 [3] 片段的各种结构。有前途的多氰基化合物是从prop-1-ene1,1,2,3,3-五甲腈衍生的盐1。在开发了一种通过丙二腈与二氧化硒在碱存在下反应制备它们的新方法后,这些盐变得容易获得[4]。1 的碱性水解伴随着杂环化生成吡咯烷酮衍生物,然后再循环生成 2,6-二氨基-3,5-二氰基吡啶-4-羧酸盐 [5]。一些异烟酸衍生物表现出生物活性;例如异烟肼和 3-氨基甲酰基-、2-氨基-和 2,5-二氨基异烟酸的衍生物,它们具有抗菌性 ISSN 1070-4280,俄罗斯有机化学杂志,2016 年,第 1 卷。52,第 9 期,第 1370-1373 页。© Pleiades Publishing, Ltd., 2016。俄语原文 © AM Khil', N.Yu。Garmash,VA Kaminskii,2016 年,发表于 Zhurnal Organicheskoi Khimii,2016 年,第 1 卷。52,第 9 期,第 1378-1381 页。
更新日期:2016-09-01
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