Furan-2-yl-methanol

A mixture of 3-(2-bromoethyl)-2-methyl-pyrido[l,2-a]pyrimidin-4-one monohydrobromide, 3-furan-2-yl-methyl-(3H-imidazo[4,5-b]pyridine-2yl)-4-piperidinyl)-amine dihydrobromide, of sodium carbonate and of N,N-dimethylformamide was stirred and heated overnight at about 70°C. The reaction mixture was poured onto water. The product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (94 6 by volume), saturated with ammonia, as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile, yielding 3-(2-(4-((3-(2-furanylmethyl)-3H-imidazo[4,5-b]pyridin-2-yl)amino)-l-piperidinyl)ethyl)-2-methyl-4H-pyrido[l,2-a]pyrimidin-4-one melting point 202°C. 

Reid and co-workers prepared a number of napthanilic quinazolinones by condensing 3-amino-2-naphthoic acid with a fuiyl imidate in methanol under thermal conditions. The desired product, 2-(furan-2-yl)benzo[g]quinazolin-4(3//)-one, was produced in 43% yield. Compounds of this class have been shown to have effective anti-cancer and antibacterial properties. 

Some furans with conjugating 2- or 3-substituents show abnormal behaviour during oxidation in methanol. Only one methoxy group is introduced after which loss of a proton restores the furan to substituent conjugation. This behaviour is shown by 2- and 3-phenyifurans and by 2-(then-2-yl)furan. 2-Methyl-4-phenyl-... 

The three-component reaction between ethyl 3-(4,5,6,7-tetrahydroindol-2-yl)pro-pynoate, DDQ, and methanol affords furan-2-on-4,5,6,7-tetrahydroindolecyclobu-tene ensemble 23 in 53% yield (Scheme 2.63) [531]. As minor products, furan-2-one isomer 24 along with bicycloheptadienone 22 has been either isolated or identified. Like in the case of benzene or acetone, the corresponding [2+2]-cycloadduct 21 is the intermediate of this reaction. 

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