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TUTCRIS

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

Tutkimustuotosvertaisarvioitu

Yksityiskohdat

AlkuperäiskieliEnglanti
Artikkeli2405
JulkaisuMolecules
Vuosikerta24
Numero13
DOI - pysyväislinkit
TilaJulkaistu - 2019
OKM-julkaisutyyppiA1 Alkuperäisartikkeli

Tiivistelmä

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.