A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-07-31 DOI:10.3762/bjoc.20.161
Ivana Weisheitelová, Radek Cibulka, Marek Sikorski, Tetiana Pavlovska
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Abstract

Functionalized 5-aryldeazaalloxazines have been successfully synthesised through a one-pot, three-component reaction involving N,N-dimethylbarbituric acid, an aromatic aldehyde and aniline. By utilizing readily available reagents, this approach opens up the opportunity for the efficient formation of a variety of 5-aryldeazaalloxazines bearing electron-donating or halogen groups. This practical method is characterised by atom economy and offers a direct route to the introduction of an aryl moiety into the C(5)-position of deazaalloxazines, thereby generating novel catalysts for photoredox catalysis without the need for subsequent purification. Thus, it significantly improves existing approaches.

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Beilstein J. Org. Chem. 2024, 20, 1831–1838. doi:10.3762/bjoc.20.161

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强效 5-aryldeazaalloxazine 光催化剂的简便三组分路线
摘要通过涉及 N,N-二甲基巴比妥酸、芳香醛和苯胺的单锅三组分反应,成功合成了官能化的 5-芳基氮杂环戊烯。通过利用现成的试剂,这种方法为高效合成各种带有电子捐赠基团或卤素基团的 5-芳基氮杂环噁嗪提供了机会。这种实用的方法具有原子经济性的特点,提供了将芳基引入脱氮氮杂环辛烷的 C(5)位的直接途径,从而生成新型光氧化催化剂,而无需进行后续纯化。Beilstein J. Org.Chem.2024, 20, 1831–1838. doi:10.3762/bjoc.20.161
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CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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