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

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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引用次数: 0

摘要

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

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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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.