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Paper | Regular issue | Vol 78, No. 10, 2009, pp.2509-2522
Published online, 1st July, 2009
DOI: 10.3987/COM-09-11760
Tetrazolium N-Aminides: Complementary Studies on Synthesis and Properties

Dietrich Moderhack* and Matthias Noreiks

*Institute of Pharmaceutical Chemistry, Technical University, Beethovenstrasse 55, D-38106 Braunschweig, Germany


Attempts are made to access the title compounds from N-amido/urei¬dotetrazoles (A, B; 1H- / 2H-system). These materials are provided by acylation of the respective N-aminotetrazoles (A in one step, B partly by hydrolysis of diacylat¬ed derivatives which are obtained directly). On treatment with excess dimethyl sul¬fate only A undergoes the necessary ring quaternization, giving rise to two isomers (ratio ca. 4 : 1); work-up with base allows isolation of the major aminide (X). This technique requires that the (slow) quaternization process be fully completed, since at pH > 7 dimethyl sulfate rapidly affects the side chain of A. Concluding experi¬ments pertain to protonation and methylation of the title compounds (X–XII).