Amines, reaction with nitro sugars

Uracil derivatives can be nitrated at C-5 under conditions that allow retention of a sugar residue at N-1 Nitration at N-3 can also be achieved N-3-nitro-compounds react with amines via an ANRORC mechanism, with displacement of nitramide and incorporation of the amine as a substituted N-3, as shown below. This seqnence has been ntilised to prepare N-3-labelled pyrimidines (31.2.2). An analogous ANRORC process takes l-(2,4-dinitrophenyl)-uracils to 1-arylamino-uracils by reaction with arylamines at room temperatnre. ... 

There are many instances in which the introduction of amines with specific substitution patterns is desired. With the abundance of structurally diverse commercially available amines from which to choose, the use of these compounds as nucleophiles is extremely valuable. While the example illustrated in Scheme 6.29 focuses on the hydrazine displacement of a secondary tosylate from a furanose sugar derivative [56], this type of reaction is easily achieved with most primary and secondary amines. Where the introduction of direct NH2 groups is desired, the best methods rely on the reduction of azides or nitro groups, or the hydrolysis (hydrazinolysis) of imides [32]. 

---