E. Benoist et al., CONVENIENT AND SIMPLIFIED APPROACHES TO N-MONOPROTECTED TRIAMINOPROPANE DERIVATIVES - KEY INTERMEDIATES FOR BIFUNCTIONAL CHELATING AGENT SYNTHESIS, Synthesis, (8), 1998, pp. 1113-1118
High yields of selectively N-protected-1,2,3-triaminopropanes (1,3 or
1,2 functionalized diamines) were obtained in 6 or 4 steps from diamin
o alcohols or aminodiols, respectively. These two multi-step procedure
s involve protection of (he amino group, substitution of the hydroxy g
roup by an azido group and selective reduction. The conditions for the
first procedure allow the preparation of various N-2-monoprotected-1,
2,3-triaminopropanes 6a, 6b, but the second one is more convenient for
obtaining N-1-Boc-1,2,3-triaminopropane 6'. These two simplified proc
edures, which provide functionalized 1,2 or 1,3 diamines easily and wi
th good overall yields, could be useful for the synthesis of bifunctio
nal chelating agents.