6533b836fe1ef96bd12a19e1

RESEARCH PRODUCT

Synthesis of 6,12-Disubstituted Methanodibenzo[

Assoah BenedictaRiihonen VesaVale João RValkonen ArtoCandeias Nuno R

subject

Pyrrolidinesself-condensationMolecular StructureenamineAcetophenonesStereoisomerism15-dioxocin2′-hydroxyacetophenoneCatalysisArticle

description

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.

yearjournalcountryeditionlanguage
2019-06-14Molecules (Basel, Switzerland)
10.3390/molecules24132405https://pubmed.ncbi.nlm.nih.gov/31261870