Nitro-substituted 2-aryl-[1,2,4]triazolo[1,5-a]azines in the reactions with C-nucleophiles

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Russian Chemical Bulletin Pub Date : 2024-06-21 DOI:10.1007/s11172-024-4251-5

M. A. Bastrakov, A. A. Kruchinin, S. A. Kolyadina, A. M. Starosotnikov

引用次数: 0

Abstract

Synthesis of nitro-substituted [1,2,4]triazolo[1,5-a]pyrimidines based on oxidative cyclization of the corresponding nitropyrimidinyl hydrazones of aromatic aldehydes was developed. The reactions of 2-aryl-6-nitro-[1,2,4]triazolo[1,5-a]pyrimidines and their structural analogs (2-aryl-6,8-dinitro-[1,2,4]triazolo[1,5-a]pyridines) with different C-nucleophiles were studied. Nucleophilic addition to the pyridine and pyrimidine rings carried out under mild base-free conditions gave new stable 1.5-dihydro-[1,2,4]triazolo [1,5-a]-pyridines and 1.5-dihydro-[1,2,4]triazolo[1,5-a]pyrimidines in the yields up to 94%.

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硝基取代的 2-芳基-[1,2,4]三唑并[1,5-a]氮杂与 C-亲核物的反应

基于相应的硝基嘧啶酰肼与芳香醛的氧化环化反应，开发了硝基取代的[1,2,4]三唑并[1,5-a]嘧啶的合成方法。研究了 2-芳基-6-硝基-[1,2,4]三唑并[1,5-a]嘧啶及其结构类似物（2-芳基-6,8-二硝基-[1,2,4]三唑并[1,5-a]吡啶）与不同 C-亲核物的反应。在温和的无碱条件下对吡啶和嘧啶环进行亲核加成，得到了新的稳定的 1.5-二氢-[1,2,4]三唑并[1,5-a]-吡啶和 1.5-二氢-[1,2,4]三唑并[1,5-a]嘧啶，产率高达 94%。

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来源期刊

Russian Chemical Bulletin 化学-化学综合

CiteScore

2.70

自引率

47.10%

发文量

257

审稿时长

3-8 weeks

期刊介绍： Publishing nearly 500 original articles a year, by leading Scientists from Russia and throughout the world, Russian Chemical Bulletin is a prominent international journal. The coverage of the journal spans practically all areas of fundamental chemical research and is presented in five sections: General and Inorganic Chemistry; Physical Chemistry; Organic Chemistry; Organometallic Chemistry; Chemistry of Natural Compounds and Bioorganic Chemistry.