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Open AccessArticle

Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins: Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones

1
Faculty of Engineering and Natural Sciences, Tampere University, Korkeakoulunkatu 8, 33101 Tampere, Finland
2
Instituto de Investigação do Medicamento (iMed.ULisboa), Faculdade de Farmácia, Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003 Lisboa, Portugal
3
Department of Chemistry, University of Jyvaskyla, P.O. Box 35, 40014 Jyväskylä, Finland
*
Authors to whom correspondence should be addressed.
Academic Editors: Paula Sério Branco and Filipa Siopa
Molecules 2019, 24(13), 2405; https://doi.org/10.3390/molecules24132405
Received: 14 June 2019 / Revised: 26 June 2019 / Accepted: 28 June 2019 / Published: 29 June 2019
(This article belongs to the Special Issue Development of New Methods of Synthesis of Heterocycles)
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. View Full-Text
Keywords: enamine; 1,5-dioxocin; self-condensation; 2′-hydroxyacetophenone enamine; 1,5-dioxocin; self-condensation; 2′-hydroxyacetophenone
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MDPI and ACS Style

Assoah, B.; Riihonen, V.; Vale, J.R.; Valkonen, A.; Candeias, N.R. Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins: Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones. Molecules 2019, 24, 2405. https://doi.org/10.3390/molecules24132405

AMA Style

Assoah B, Riihonen V, Vale JR, Valkonen A, Candeias NR. Synthesis of 6,12-Disubstituted Methanodibenzo[b,f][1,5]dioxocins: Pyrrolidine Catalyzed Self-Condensation of 2′-Hydroxyacetophenones. Molecules. 2019; 24(13):2405. https://doi.org/10.3390/molecules24132405

Chicago/Turabian Style

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, no. 13: 2405. https://doi.org/10.3390/molecules24132405

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