Eosin Y-catalyzed visible-light-mediated aerobic transformation of pyrazolidine-3-one derivatives

Petek, Nejc (author), Grošelj, Uroš (author), Svete, Jurij (author), Požgan, Franc (author), Kočar, Drago (author), Štefane, Bogdan (author)

By utilizing an underexplored reactivity of N1-substituted pyrazolidine-3-ones, we developed a visible-light-induced aerobic oxidation of N1-substituted pyrazolidine-3-one derivatives yielding the corresponding azomethine imines. The resulting azomethine imines can be further reacted with ynones in situ under copper catalyzed [3 + 2] cycloaddition reaction conditions yielding the corresponding pyrazolo[1,2-a]pyrazoles in good yields. The methodology can be extended to other 1-aryl-substituted pyrazolidinones which undergo endocyclic oxidation deriving the corresponding pyrazolones as single products.

• Language: English
• Keywords: pyrazolidine-3-ones, eosin Y, visible light, photoredox catalysis
• Work type: Article
• Typology: 1.01 - Original Scientific Article
• Organization: FKKT - Faculty of Chemistry and Chemical Technology
• Publication status: Published
• Publication version: Version of Record
• Year: 2020
• Number of pages: 10 str.
• Numbering: Vol. 10, iss. 9, art. 981
• PID: 20.500.12556/RUL-134247
• UDC: 547.77:544.47
• ISSN on article: 2073-4344
• DOI: 10.3390/catal10090981
• COBISS.SI-ID: 27805187
• Publication date in RUL: 03.01.2022

Record is a part of a journal

• Title: Catalysts
• Shortened title: Catalysts
• Publisher: MDPI AG
• ISSN: 2073-4344
• COBISS.SI-ID: 519958297

Licences

• License: CC BY 4.0, Creative Commons Attribution 4.0 International
• Link: http://creativecommons.org/licenses/by/4.0/
• Description: This is the standard Creative Commons license that gives others maximum freedom to do what they want with the work as long as they credit the author.
• Licensing start date: 01.09.2020

Secondary language

• Language: Slovenian
• Keywords: pirazolidin-3-oni, eosin Y, vidna svetloba, fotoredoks kataliza

Projects

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0179
• Name: Napredna organska sinteza in kataliza