A1 Journal article (refereed)
Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins : Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones (2019)
Assoah, Benedicta; Riihonen, Vesa; Vale, João R.; Valkonen, Arto; Candeias, Nuno R. (2019). Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins : Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones. Molecules, 24 (13), 2405. DOI: 10.3390/molecules24132405
JYU authors or editors
Publication details
All authors or editors: Assoah, Benedicta; Riihonen, Vesa; Vale, João R.; Valkonen, Arto; Candeias, Nuno R.
Journal or series: Molecules
eISSN: 1420-3049
Publication year: 2019
Volume: 24
Issue number: 13
Article number: 2405
Publisher: MDPI
Publication country: Switzerland
Publication language: English
DOI: https://doi.org/10.3390/molecules24132405
Open Access: Publication published in an open access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/65113
Abstract
The preparation of unprecedented 6,12-disubstituted methanodibenzo[b,f][1,5]dioxocins from pyrrolidine catalyzed self-condensation of 2′-hydroxyacetophenones is herein described. This method provides easy access to this highly bridged complex core, resulting in construction of two C–O and two C–C bonds, a methylene bridge and two quaternary centers in a single step. The intricate methanodibenzo[b,f][1,5]dioxocin compounds were obtained in up to moderate yields after optimization of the reaction conditions concerning solvent, reaction times and the use of additives. Several halide substituted methanodibenzo[b,f][1,5]dioxocins could be prepared from correspondent 2′-hydroxyacetophenones.
Keywords: organic compounds; chemical synthesis
Free keywords: enamine; 1,5-dioxocin; self-condensation; 2′-hydroxyacetophenone
Contributing organizations
Related projects
- Robust S...I+...S Halogen Bonded Supramolecular Assemblies (research costs)
- Valkonen, Arto
- Academy of Finland
Ministry reporting: Yes
Reporting Year: 2019
JUFO rating: 1