Abstract

An interaction of 6-aryl-1,2,4-triazine-5-carbonitriles with 2‑amino-4-aryl-substituted thiazoles and oxazoles has been studied. The difference in the reactivity of these aminoheterocycles depending on the presence of an oxygen or a sulfur atom in their composition has been demonstrated. Previously, the 4-aryl-3-hydroxy-2,2′-bipyridines were obtained as products of aza-Diels−Alder reaction between 6-aryl-3-(2-pyridyl)-1,2,4-triazine-5-carbonitriles and 2-amino-4-aryloxazoles. It was shown that the reaction of 6-aryl-1,2,4-triazine-5-carbonitriles with 2-aminothiazoles led to the products of ipso-substitution of cyano group. The aza-Diels−Alder reaction of these compounds with 2,5-norbornadiene gave (2,2′-bi)pyridines with the 2-aminothiazolyl at alpha-position.

中文翻译：

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2-氨基-(4-芳基)-取代的噻唑和恶唑与 5-氰基-1,2,4-三嗪的相互作用

摘要

研究了 6-aryl-1,2,4-triazine-5-carbonitriles 与 2‑amino-4-aryl-substituted 噻唑和恶唑的相互作用。这些氨基杂环的反应性差异取决于其组成中氧或硫原子的存在。以前，4-aryl-3-hydroxy-2,2'-bipyridines 是作为 6-aryl-3-(2-pyridyl)-1,2,4-triazine-5 之间的 aza-Diels-Alder 反应的产物获得的-腈和 2-氨基-4-芳基恶唑。结果表明，6-aryl-1,2,4-triazine-5-carbonitriles 与 2-aminothiazoles 的反应导致了氰基ipso取代的产物。这些化合物与 2,5-降冰片二烯的氮杂-狄尔斯-阿尔德反应生成 (2,2'-双) 吡啶，其 2-氨基噻唑基位于 α 位。