Double spirocyclization of arylidene-∆$^2$-pyrrolin-4-ones with 3-isothiocyanato oxindoles

Ričko, Sebastijan (author), Testen, Žan (author), Ciber, Luka (author), Požgan, Franc (author), Štefane, Bogdan (author), Brodnik, Helena (author), Svete, Jurij (author), Grošelj, Uroš (author)

Arylidene-∆$^2$-pyrrolin-4-ones undergo organocatalyzed double spirocyclization with 3-isothiocianato oxindoles in a domino 1,4/1,2-addition sequence. The products contain three contiguous stereocenters (ee up to 98%, dr up to 99:1, 12 examples). The absolute configuration of the major diastereomer was determined by single crystal X-ray analysis. Along with heterocyclic Michael acceptors based on oxazolone, isoxazolone, thiazolidinone, pyrazolone, and pyrimidinedione, the reported results display the applicability of unsaturated ∆$^2$-pyrrolin-4-ones (pyrrolones) for the organocatalyzed construction of 3D-rich pyrrolone-containing heterocycles.

• Language: English
• Keywords: organocatalysis, pyrrolones, spiroheterocyclization, 3-isothiocyanato oxindoles, cascade reaction, spiro compounds
• 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: 13 str.
• Numbering: Vol. 10, iss. 10, art. 1211
• PID: 20.500.12556/RUL-134725
• UDC: 547.74
• ISSN on article: 2073-4344
• DOI: 10.3390/catal10101211
• COBISS.SI-ID: 33665795
• Publication date in RUL: 27.01.2022

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: 19.10.2020

Secondary language

• Language: Slovenian
• Keywords: organokatalizatorji, piroloni, spiroheterociklizacija, 3-izotiocianato oksindoli, kaskadne reakcije, spiro spojine

Projects

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

• Funder: ARRS - Slovenian Research Agency
• Project number: P1-0175
• Name: Napredna anorganska kemija