Synthesis of 6,12-disubstituted methanodibenzo[b,f ][1,5]dioxocins: Pyrrolidine catalyzed self-condensation of 2′-Hydroxyacetophenones

Benedicta Assoah; Vesa Riihonen; João R. Vale; Arto Valkonen; Nuno R. Candeias

doi:10.3390/molecules24132405

Synthesis of 6,12-disubstituted methanodibenzo[b,f ][1,5]dioxocins: Pyrrolidine catalyzed self-condensation of 2′-Hydroxyacetophenones

Benedicta Assoah, Vesa Riihonen, João R. Vale, Arto Valkonen, Nuno R. Candeias

Materials Science and Environmental Engineering

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3 Citations (Scopus)

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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.

Original language	English
Article number	2405
Journal	Molecules
Volume	24
Issue number	13
DOIs	https://doi.org/10.3390/molecules24132405
Publication status	Published - 2019
Publication type	A1 Journal article-refereed

Keywords

1,5-dioxocin
20-hydroxyacetophenone
Enamine
Self-condensation

Publication forum classification

Publication forum level 1

ASJC Scopus subject areas

Analytical Chemistry
Chemistry (miscellaneous)
Molecular Medicine
Pharmaceutical Science
Drug Discovery
Physical and Theoretical Chemistry
Organic Chemistry

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10.3390/molecules24132405Licence: CC BY

molecules-24-02405
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. https://creativecommons.org/licenses/by/4.0/
Final published version, 1.26 MBLicence: CC BY

http://urn.fi/URN:NBN:fi:tty-201908282044Licence: CC BY

CCDC 1922829: Experimental Crystal Structure Determination
Assoah, B. (Creator), Riihonen, V. (Contributor), Vale, J. R. (Contributor), Valkonen, A. (Contributor) & Candeias, N. R. (Contributor), Cambridge Crystallographic Data Centre, 13 Jun 2019
DOI: 10.5517/ccdc.csd.cc22jvr7
Dataset

Cite this

@article{66ae18c83a9a46768ac2a9fe2045c7b1,

title = "Synthesis of 6,12-disubstituted methanodibenzo[b,f ][1,5]dioxocins: Pyrrolidine catalyzed self-condensation of 2′-Hydroxyacetophenones",

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 = "1,5-dioxocin, 20-hydroxyacetophenone, Enamine, Self-condensation",

author = "Benedicta Assoah and Vesa Riihonen and Vale, {Jo{\~a}o R.} and Arto Valkonen and Candeias, {Nuno R.}",

note = "EXT={"}Valkonen, Arto{"} INT=msee,{"}Riihonen, Vesa{"} INT=msee,{"}Vale, Jo{\~a}o R.{"}",

year = "2019",

doi = "10.3390/molecules24132405",

language = "English",

volume = "24",

journal = "Molecules",

issn = "1420-3049",

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TY - JOUR

T1 - Synthesis of 6,12-disubstituted methanodibenzo[b,f ][1,5]dioxocins

T2 - Pyrrolidine catalyzed self-condensation of 2′-Hydroxyacetophenones

AU - Assoah, Benedicta

AU - Riihonen, Vesa

AU - Vale, João R.

AU - Valkonen, Arto

AU - Candeias, Nuno R.

N1 - EXT="Valkonen, Arto" INT=msee,"Riihonen, Vesa" INT=msee,"Vale, João R."

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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.

KW - 1,5-dioxocin

KW - 20-hydroxyacetophenone

KW - Enamine

KW - Self-condensation

U2 - 10.3390/molecules24132405

DO - 10.3390/molecules24132405

M3 - Article

C2 - 31261870

AN - SCOPUS:85068362408

SN - 1420-3049

VL - 24

JO - Molecules

JF - Molecules

IS - 13

M1 - 2405

ER -

Synthesis of 6,12-disubstituted methanodibenzo[b,f ][1,5]dioxocins: Pyrrolidine catalyzed self-condensation of 2′-Hydroxyacetophenones

Abstract

Keywords

Publication forum classification

ASJC Scopus subject areas

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Datasets

CCDC 1922829: Experimental Crystal Structure Determination

Cite this