Three-component domino reactions in the synthesis of polyfluoroalkyl-containing tetrahydropyrido[2,1-b]quinazolines

IF 1.7 4区 化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Russian Chemical Bulletin Pub Date : 2024-12-06 DOI:10.1007/s11172-024-4413-5
S. O. Kushch, M. V. Goryaeva, Ya. V. Burgart, M. A. Ezhikova, M. I. Kodess, P. A. Slepukhin, V. I. Saloutin
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Abstract

The three-component reaction of polyfluoroalkyl-3-oxo esters with α,β-unsaturated aldehydes and 2-(aminomethyl)aniline afforded 8-(polyfluoro-1-hydroxyalkyl)-6,7,8,11-tetrahydro-9H-pyrido[2,1-b]quinazolin-9-ones upon heating; under mild conditions, this reaction gave bicyclic dihydroquinazoline intermediates, CF3 derivatives of which exist in the form of bases and their C2F5 analogues exist in the form of salts. The diastereomeric and tautomeric structures of the new heterocycles were studied by 1H, 19F, and 13C NMR spectroscopy, IR spectroscopy, and X-ray diffraction. A domino mechanism for their formation was proposed.

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合成含多氟烷基四氢吡啶[2,1-b]喹唑啉的三组分多米诺反应
多氟烷基-3-氧基酯与α,β-不饱和醛和2-(氨基甲基)苯胺的三组分反应加热后得到8-(多氟-1-羟基烷基)-6,7,8,11-四氢- 9h -吡啶[2,1-b]喹唑啉-9-酮;在温和条件下,该反应生成双环双氢喹唑啉中间体,CF3衍生物以碱的形式存在,C2F5类似物以盐的形式存在。通过1H、19F、13C NMR、IR、x射线衍射等手段对新杂环的非对映体和互变异构结构进行了研究。提出了它们形成的多米诺骨牌机制。
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来源期刊
Russian Chemical Bulletin
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.
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