Synthesis of 6,12-disubstituted methanodibenzo[b,f ][1,5]dioxocins: Pyrrolidine catalyzed self-condensation of 2′-Hydroxyacetophenones
Research output: Contribution to journal › Article › Scientific › peer-review
Details
| Original language | English |
|---|---|
| Article number | 2405 |
| Journal | Molecules |
| Volume | 24 |
| Issue number | 13 |
| DOIs | |
| Publication status | Published - 2019 |
| Publication type | A1 Journal article-refereed |
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.
ASJC Scopus subject areas
Keywords
- 1,5-dioxocin, 20-hydroxyacetophenone, Enamine, Self-condensation