Bis(1,3,4-thiadiazolo)-1,3,5-triazinium halides 3; Synthesis of guanidyl-functionalized 1,4,8,11-tetraazacyclotetradecanes and tris(2-amino-ethyl)amines: Application of a novel rearrangement

The reaction of bis(l,3,4-thiadiazolo)-1,3,5-triazinium (or "5/6/5") halide s 1 with 1,4,8,11-tetraazacyclotetradecane (2) and tris(2-aminoethyl)-amine (6) yields new N-functionalized cyclams (3a-d) as well as the complex tert iary amine 7. All of the NH or NH, groups in 2 and 6 are transformed into ( chiral) guanidyl moieties. The structure of a representative of 3 was confi rmed by single crystal X-ray analysis.