A1 Journal article (refereed)
Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins : Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones (2019)

Assoah, B., Riihonen, V., Vale, J. R., Valkonen, A., & Candeias, N. R. (2019). Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins : Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones. Molecules, 24(13), Article 2405. https://doi.org/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

Publication open access: Openly available

Publication channel open access: 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

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Related projects

Ministry reporting: Yes

Reporting Year: 2019

JUFO rating: 1