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嘧啶并[4,5 - ]喹啉二酮的合成与甲酰化：超声辅助反应

Synthesis of pyrimido[4,5-]quinolindiones and formylation: ultrasonically assisted reactions.

作者信息

Trilleras Jorge, Charris-Molina Andrés, Pérez-Gamboa Alfredo, Acosta-Guzman Paola, Quiroga Jairo

机构信息

Programa de Química, Facultad de Ciencias Básicas, Universidad del Atlántico, Puerto Colombia 81007, Colombia.

Facultad de Ciencias Exactas y Naturales, Departamento de Química Inorgánica Analítica y Química Física, Universidad de Buenos Aires, Buenos Aires C1428EGA, Argentina.

出版信息

R Soc Open Sci. 2024 Mar 6;11(3):231128. doi: 10.1098/rsos.231128. eCollection 2024 Mar.

DOI:10.1098/rsos.231128
PMID:38455992
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10915537/
Abstract

Ultrasound-assisted synthesis of pyrimido‌quinolindione derivatives via a multicomponent reaction and subsequent formylation with Vilsmeier-Haack reagent were performed. Compounds were prepared by a one-pot method from aminopyrimidinones, dimedone and aromatic aldehydes through a Mannich-type reaction sequence, and then functionalized under ultrasound irradiation and Vilsmeier-Haack conditions to give β-chlorovinylaldehyde products. Ultrasonically assisted reactions, experimental simplicity, good yields without using metallic catalysts and the control of hazardous material release are features of this simple procedure.

摘要

通过多组分反应超声辅助合成嘧啶并喹啉二酮衍生物，随后用Vilsmeier-Haack试剂进行甲酰化反应。化合物由氨基嘧啶酮、二氢嘧啶酮和芳香醛通过一锅法经曼尼希型反应序列制备，然后在超声辐射和Vilsmeier-Haack条件下进行官能化反应，得到β-氯代乙烯基醛产物。超声辅助反应、实验简单、无需使用金属催化剂即可获得良好产率以及控制有害物质释放是此简单方法的特点。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6b8/10915537/90b94bf49ec4/rsos.231128.f009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6b8/10915537/90b94bf49ec4/rsos.231128.f009.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6b8/10915537/5d10a8983cbd/rsos.231128.f006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6b8/10915537/600432a3e3f9/rsos.231128.f007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6b8/10915537/c80c8380b6a4/rsos.231128.f008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b6b8/10915537/90b94bf49ec4/rsos.231128.f009.jpg

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本文引用的文献

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Docking, Synthesis and Evaluation of the Antifungal Activity of Pyrimido [4,5-b]quinolins.嘧啶并[4,5-b]喹啉的对接、合成及抗真菌活性评价
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Ultrasound-assisted synthesis of heterocyclic compounds.超声辅助杂环化合物的合成。
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Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions.无配体铜催化的串联反应合成嘧啶并喹啉。
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Multicomponent reaction for the first synthesis of 2,2-dialkyl- and 2-alkyl-2-aralkyl-5,6-diaryl-2H-1,3-thiazines as scaffolds for various 3,4-dihydro-2H-1,3-thiazine derivatives.首次合成2,2 - 二烷基 - 和2 - 烷基 - 2 - 芳烷基 - 5,6 - 二芳基 - 2H - 1,3 - 噻嗪作为各种3,4 - 二氢 - 2H - 1,3 - 噻嗪衍生物支架的多组分反应。
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(5RS)-5-(4-Methoxyphenyl)-2-(methylsulfanyl)benzo[g]pyrimido[4,5-b]quinoline-4,6,11(3H,5H,12H)-trione, with Z' = 3, forms a three-dimensional hydrogen-bonded framework containing five types of hydrogen bond.（5RS）-5-（4-甲氧基苯基）-2-（甲硫基）苯并[g]嘧啶并[4,5-b]喹啉-4,6,11（3H，5H，12H）-三酮，Z' = 3，形成了一个包含五种氢键的三维氢键框架。
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Synthesis, in vitro antimicrobial and in vivo antitumor evaluation of novel pyrimidoquinolines and its nucleoside derivatives.新型嘧啶并喹啉及其核苷衍生物的合成、体外抗菌和体内抗肿瘤活性评价。
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In vitro anticancer screening and radiosensitizing evaluation of some new quinolines and pyrimido[4,5-b]quinolines bearing a sulfonamide moiety.含有磺酰胺基的一些新型喹啉和嘧啶并[4,5-b]喹啉的体外抗癌筛选和放射增敏评价。
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Novel quinolines and pyrimido[4,5-b]quinolines bearing biologically active sulfonamide moiety as a new class of antitumor agents.新型含生物活性磺酰胺基的喹啉和嘧啶并[4,5-b]喹啉类抗肿瘤药物。
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