NITROSATION OF PHENOLIC SUBSTRATES UNDER MILDLY BASIC CONDITIONS - SELECTIVE PREPARATION OF P-QUINONE MONOOXIMES AND THEIR ANTIVIRAL ACTIVITIES

Nitrosation of 3-methoxyphenol and 1-naphthol were examined under both acidic (NaNO2-EtCO(2)H-H2O) and basic (i-AmNO2-K2CO3-DMF) conditions, Acidic nitrosations afforded ortho-directed products, whereas para-di rected nitrosations were observed under basic conditions to yield p-qu inone monooximes. The basic para-directed nitrosation was further exam ined using 15 phenols, two naphthols, and four phenolic heterocyclics, A one-pot operation of the basic nitrosation followed by methylation with dimethyl sulfate gave the corresponding methyl ethers in high yie ld, Two p-quinone monooximes derived from 3-methoxyphenol and 8-hydrox yquinoline showed a moderate activity against HSV-1, and the latter ox ime was also effective against HSV-2, On the other hand, p-quinone mon ooximes derived from methyl salicylate, 1-naphthol, 7-hydroxy-2-methyl benzo[b]-furan, and 8-hydroxycoumarin showed the comparable activity t o that of DDI against HIV-1.