REACTIONS OF RELEVANCE TO THE CHEMISTRY OF AMINOGLYCOSIDE ANTIBIOTICS .10. ALPHA-ALKYLATION OF PRIMARY AMINES

Alkylation at the .alpha.-carbon atom of primary amines can be conveniently accomplished by a sequence involving formation of the corresponding azoxy-derivative, alkylation with an alkyl-lithium and subsequent cleavage of the .alpha.-alkylated azo-compound. Improved procedures are described for the preparation of unsymmetrical azoxy-derivatives. The scope of the reductive alkylation of azoxy-compounds was considerably extended. Chain extension by alkylation at the .alpha.-carbon atom of amines is a desirable reaction, particularly for the modification of biological activity in aminoglycoside antibiotics.