Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins : Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones
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
© 2019 by the authors.
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.
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Related funder(s)Academy of Finland
Funding program(s)Research costs of Academy Research Fellow, AoF
Additional information about fundingThis research was funded by Academy of Finland, grant numbers 326487, 326486 and 314343. The APC was funded by 326486.
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