Structural Chemistry & Crystallography Communication

A Facile and Commodius method for the Synthesis of 1,8-dihydro-as-indacene

IThe synthesis of 1,8-dihydro-as-indacene was prepared in 8 steps starting from alkylation of   2-methyl-furan with formaldehyde and substituted with ethylamine hydrochloride to gives a isolated mixture of 5-methyl-2-furfuryldimethylamine, the amine was quaternized by treating with methyl iodide and anion exchange using Ag2O resulted in the intermediate ammonium hydroxide subsequently without isolation, to removing the water by hydrolysis process. The hydroxide was pyrolyzed by a transformation of furanocyclophane (4a). Photooxidation of the 4a in methanol gives a mixture of oxy diketone (5a) and a peroxidic compound, either a methoxy diketone. Sodium iodide in acetic acid reduces the peroxide to give pure 5a, which is dehydrated by sodium carbonate to (6a) and a purified the diketone in column chromatographic method to gave a pure 6a. sodium borohydride reduction, acetylation(7a) and pyrolysis yield dihydro-as-indacene (8a). 

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