The Study On Reformatsky-Type Reaction Of Sulfonylimines

Reformatsky-Type reaction of imines is an important reaction in the preparation ofβ-amino carbonyl compounds. But Reformatsky-Type reactions of imines withα-bromoacetamides were little reported. A series of N-sulfonylimines andα-bromoacetamides were prepared. On the basis of the above works, the reactions ofα-bromoacetamides with N-sulfonylimines in the presece of zinc powder were studied. To get the optimized condition, the effect of solvent polarity, temperature, time and the proportion of the reactants were examined. All products are unknown compounds and their structures have been determined by IR, 1H NMR and element analysis.Furthermore, the X-ray crystal analysis of the compound, namely, 3-(2,4-dichlorophenyl)-N,N-diethyl-3-(4-methylphenylsulfonylamino)propanamide, also confirms the structure of the product.A potential additional mechanism was proposed. A transition state of six-mumbered ring was formed through the addition of the organozinc reagents ofα-bromoacetamides with N-sulfonylimines.