5-(三烷基)硅基戊-1-烯-4-炔-3-酮与肼的反应:合成含唑基发光物质的原始途径

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Synthesis-Stuttgart Pub Date : 2023-11-13 DOI:10.1055/s-0043-1763601
Alexander A. Golovanov, Ivan S. Odin, Kareem V. Gordon, Radik N. Itakhunov, Dmitry M. Gusev, Sergey A. Sokov, Anna V. Vologzhanina, Stanislav A. Grabovskiy, Ilya M. Sosnin, Anton I. Ukolov, Olga I. Orlova, Vladimir A. Lazarenko, Pavel V. Dorovatovskii, Darina D. Darmoroz, Anastasiia O. Piven, Tetiana Orlova
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引用次数: 0

摘要

摘要以肼与三烷基硅基取代的交叉共轭烯酮(p- 1-en-4- n-3-one)的选择性反应为基础,本文提出了合成乙基吡唑啉、吡唑以及含有吡唑啉、异恶唑、噻吩、噻唑、苯并[d]噻唑和苯并[d]咪唑结构片段的组合多杂环的多取代发光衍生物的常用方法。在与肼及其单取代芳香族和杂芳香族衍生物反应时,上述在三键上含有Me3Si、Et3Si和t-BuMe2Si基团的-1-en-4-yn-3- 1反应得到3-(三烷基硅基)乙基吡唑啉。在与腈氧化物进行脱硅基化和1,3-偶极环加成之后,3-(三烷基硅基)乙基吡唑啉形成了组合多杂环衍生物。由此,建立了以交叉共轭炔酮、芳基肼和α-氯苯醛肟为原料,一锅法合成含吡唑啉类异恶唑的方法。对合成的唑类衍生物的环缩合机理和发光性能进行了研究。
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Reactions of 5-(Trialkyl)silylpent-1-en-4-yn-3-ones with Hydrazines: Original Synthetic Routes to Luminescent Substances Containing Azole Motifs
Abstract On the basis of the selective reactions of hydrazines with trialkylsilyl-substituted cross-conjugated enynones (pent-1-en-4-yn-3-ones) as fundamental building blocks, this work presents the developed common methodology for the synthesis of polysubstituted luminescent derivatives of acetylenic pyrazolines, pyrazoles, and combined polyheterocycles containing structural fragments from pyrazolines, isoxazoles, thiophenes, thiazoles, benzo[d]thiazoles, and benzo[d]imidazoles. In reactions with hydrazine and its monosubstituted aromatic and heteroaromatic derivatives, the mentioned pent-1-en-4-yn-3-ones, containing Me3Si, Et3Si, and t-BuMe2Si groups at the triple bond, give 3-(trialkylsilyl)ethynylpyrazolines. Following stages of desilylation and 1,3-dipolar cycloaddition with nitrile oxides, the 3-(trialkylsilyl)ethynylpyrazolines provide the formation of combined polyheterocyclic derivatives. Thus, a one-pot synthetic route to pyrazoline-containing isoxazoles from cross-conjugated enynones, arylhydrazines, and α-chlorobenzaldoximes has been developed. Some aspects of cyclocondensation mechanism and luminescent properties of synthesized azoles derivatives were examined.
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来源期刊
Synthesis-Stuttgart
Synthesis-Stuttgart 化学-有机化学
CiteScore
4.50
自引率
7.70%
发文量
435
审稿时长
1 months
期刊介绍: SYNTHESIS is an international full-paper journal devoted to the advancement of the science of chemical synthesis. It covers all fields of organic chemistry involving synthesis, including catalysis, organometallic, medicinal, biological, and photochemistry, but also related disciplines. SYNTHESIS provides dependable research results with detailed and reliable experimental procedures and full characterization of all important new products as well as scientific primary data.
期刊最新文献
Dealkenylative Functionalizations: Conversion of Alkene C(sp3)-C(sp2) Bonds into C(sp3)-X Bonds via Redox-Based Radical Processes. Aryl Annulation: A Powerful Simplifying Retrosynthetic Disconnection. Improved Syntheses of an Arseno-Fatty Acid (As-FA 362) and an Arseno-Hydrocarbon (As-HC 444). SYNFORM ISSUE 2023/12 Linked PDF of Table of Contents
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