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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/b6b8/10915537/2c9e75f36eed/rsos.231128.f001.jpg

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本文引用的文献

1
Docking, Synthesis and Evaluation of the Antifungal Activity of Pyrimido [4,5-b]quinolins.
Iran J Pharm Res. 2020 Winter;19(1):251-259. doi: 10.22037/ijpr.2020.1101010.
2
Ultrasound-assisted synthesis of heterocyclic compounds.
Mol Divers. 2020 Aug;24(3):771-820. doi: 10.1007/s11030-019-09964-1. Epub 2019 Jun 4.
3
Synthesis of Pyrimidine Fused Quinolines by Ligand-Free Copper-Catalyzed Domino Reactions.
J Org Chem. 2018 Apr 6;83(7):3624-3632. doi: 10.1021/acs.joc.7b03272. Epub 2018 Mar 23.
4
Recent developments on ultrasound-assisted one-pot multicomponent synthesis of biologically relevant heterocycles.
Ultrason Sonochem. 2017 Mar;35(Pt A):15-35. doi: 10.1016/j.ultsonch.2016.10.010. Epub 2016 Oct 14.
5
A three-component reaction for rapid access to underexplored 1,3-thiazine-2-thiones.
Org Biomol Chem. 2015 Jul 14;13(26):7223-9. doi: 10.1039/c5ob00377f. Epub 2015 Jun 8.
6
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.
Org Biomol Chem. 2014 Jul 28;12(28):5168-81. doi: 10.1039/c4ob00866a.
7
(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.
Acta Crystallogr C Struct Chem. 2014 Jan;70(Pt 1):50-4. doi: 10.1107/S2053229613032956. Epub 2013 Dec 14.
8
Synthesis, in vitro antimicrobial and in vivo antitumor evaluation of novel pyrimidoquinolines and its nucleoside derivatives.
Eur J Med Chem. 2011 Jan;46(1):21-30. doi: 10.1016/j.ejmech.2010.09.071. Epub 2010 Oct 8.
9
In vitro anticancer screening and radiosensitizing evaluation of some new quinolines and pyrimido[4,5-b]quinolines bearing a sulfonamide moiety.
Eur J Med Chem. 2010 Sep;45(9):3677-84. doi: 10.1016/j.ejmech.2010.05.014. Epub 2010 May 12.
10
Novel quinolines and pyrimido[4,5-b]quinolines bearing biologically active sulfonamide moiety as a new class of antitumor agents.
Eur J Med Chem. 2010 Feb;45(2):738-44. doi: 10.1016/j.ejmech.2009.11.021. Epub 2009 Nov 18.

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