TETRAZOLIUM N-AMINIDES: COMPLEMENTARY STUDIES ON SYNTHESIS AND PROPERTIES

摘要

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 diacylated derivatives which are obtained directly). On treatment with excess dimethyl sulfate 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 experiments pertain to protonation and methylation of the title compounds (X-XII).