REACTION OF D-GALACTOSE PHENYLHYDRAZONE WITH NITROALKENES:SYNTHESIS OF PENTAHYDROXYPENTYLPYRAZOLES

Article abstract of DOI:10.1016/0008-6215(88)80058-2

D-Galactose phenylhydrazone reacts with 1- and 2-substituted and 1,2-disubstituted nitroalkenes, with loss of the nitro group, to give moderate yields of 3-(D-galacto-pentitol-1-yl)-1-phenylpyrazoles variously substituted at positins 4, 5 and a mechanism is proposed.Acetylation of these products affords pentaacetates and periodate oxidation gave the corresponding 1-phenylpyrazole-3-carbaldehyde derivatives, some of which were oxidised to the carboxylic acids.U.v., i.r., and n.m.r. data confirm the proposed structures.