Journal
SYNTHESIS-STUTTGART
Volume 53, Issue 3, Pages 569-573Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1707372
Keywords
as-indacene; [6,6]-cycloaddition; polycyclic bridged ligand; bimetallic ligand; Mannich condensation; Hoffmann elimination
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Funding
- Fondo Nacional de Desarrollo Cientifico y Tecnologico, Chile (FONDECYT) [1161297, EQM120021, EQM130032, EQM150102]
- Pontificia Universidad Catolica de Chile (PUC) [3913-541-81]
- Scheduled Tribes Welfare Department, Government of Karnataka, India
- Severo Ochoa Program, Ministerio de Economia y Competitividad (MINECO) [SEV-2015-0496]
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The contribution presents an updated synthetic route to 3,6-dihydro-as-indacene and characterization of all intermediates. The title compound is obtained through a series of reactions starting from 2-methylfuran, with the structure confirmed by X-ray diffraction.
This contribution describes an updated synthetic route to 3,6-dihydro-as-indacene along with full characterization of all intermediates. The title compound is prepared by Mannich condensation of 2-methylfuran with formaldehyde and dimethylamine hydrochloride, quaternization of the resulting amine with methyl iodide, and conversion into the ammonium hydroxide salt by treatment with silver oxide in water. Subsequent Hoffmann elimination and [6,6]-cycloaddition through pyrolysis produces a furanocyclophane, which after photooxidation, intramolecular cycloaddition, and dehydration with sodium carbonate affords 2,3,6,7-tetrahydro-1,8-dione-as-indacene. Reduction of this diketone gives a mixture of alcohols, which after dehydration under slightly basic or acidic conditions produces 3,6-dihydro-as-indacene. The structure is confirmed by X-ray diffraction, and all intermediates are characterized by means of H-1 and C-13 NMR spectroscopy.
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