The Study On New Reactions Of α-Alkoxylamidoalkylphenyl Sulfones Induced By Zinc

The Mannich condensations of carbamates, sodium sulfinates with alkyl or aromatic aldehydes affordα-alkoxylamidoalkylmethylphenyl sulfones orα-alkoxylamidoaromaticmethylphenyl sulfones. These organic synthetic intermediates which are usually stable solids at room temperature for several days to months can react with various nucleophiles. Thus, such reactions contribute to a practical method for the preparation of compounds containing nitrogen. Zinc is a cheap, easily available and nontoxic metal. Both easy formation of carbon–nitrogen bond and reasonable reactivity make organozinc reagents useful in organic synthesis. The reactions ofα-alkoxylamidoalkylphenyl sulfones withα-bromocarbonyl compounds produceβ-alkoxylamidocarbonyl compounds.We focus on the reactions ofα-alkoxylamidoaromaticmethylphenyl sulfones withα-bromoacetophenone induced by zinc in THF and the expectedβ–alkoxylamido ketones are obtained. Besides, we attemp to study on the reactions ofα-alkoxylamidoaromaticmethylphenyl sulfones with ethyl bromoacetate andα-alkoxylamidoalkylphenyl sulfones withα-bromoacetamides. A possible reaction mechanism is proposed about an elimination–addition process. We optimize the reaction conditions by means of screening solvent, temperature, reaction time and proportion of the reactants. IR spectrum, 1HNMR spectrum , 13CNMR spectrum and MS spectrum confirm the structures of the expected products.The study extends the application ofα-alkoxylamidoalkylphenyl sulfones. The reaction condition is mild without any special catalyst and technically simple.