Polyamines, structurally related to putrescines and spermidines, are easily obtainable via hydroaminomethylation of methylallylphthalimide with primary or secondary amines. In addition, hydroaminomethylation of monoolefins with urea as a synthetic equivalent for ammonia, in contrast to other methods (e.g. the alkylation of ammonia or ammonium salts), allows selective synthesis of symmetric tertiary amines. By combining both methods dendrons and dendrimer cores are conveniently obtained.
A general concept for a versatile convergent synthesis of polynitrile and/or polyamine dendrimers has been developed by applying Vögtle's procedure in combination with the tandem hydroformylation/reductive amination sequence, known as hydroaminomethylation. In this approach, first Vögtle's procedure is used to generate the desired dendron,
A new method for the synthesis of polyamines via hydroaminomethylation of methylallylphthalimide (I) with primary and secondary amines is presented. Product (VII) is used as starting material for the preparation of the dendrons and dendritic cores. With urea as the ammonia source, symmetrical tertiary amines [cf. (IX)] are obtained in one step without any reduction. -(MUELLER, K.-S.; KOC, F.; RICKEN, S.; EILBRACHT*, P.; Org.
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