Tetrazoles methylation

The Methyl Tetrazoles and Derivatives 1-Methyl Tetrazole [Methyl-l-tetrazol (Ger)]. 

Despite the weak basicity of isoxazoles, complexes of the parent methyl and phenyl derivatives with numerous metal ions such as copper, zinc, cobalt, etc. have been described (79AHC(25) 147). Many transition metal cations form complexes with Imidazoles the coordination number is four to six (70AHC(12)103). The chemistry of pyrazole complexes has been especially well studied and coordination compounds are known with thlazoles and 1,2,4-triazoles. Tetrazole anions also form good ligands for heavy metals (77AHC(21)323). 

For both azole and benzazole rings the introduction of further heteroatoms into the ring affects the ease of quaternization. In series with the same number and orientation of heteroatoms, rate constants increase in the order X = 0requires stronger reagents and conditions methyl fluorosulfonate is sometimes used (78AHC(22)71). The 1-or 2-substituted 1,2,3-triazoles are difficult to alkylate, but methyl fluorosulfonate succeeds (7IACS2087). 

Halogen atoms at the 5-position of tetrazoles are reactive and easily replaced by nucleophiles. 5-Bromo-l-methyltetrazole is significantly more reactive than the 2-methyl isomer (77AHC(21)323). 

A similar intramolecular trapping of the intermediate (511) from the photolysis of the corresponding methyl tetrazole-l,5-dicarboxylate (510) gave methyl 5-methoxy-l,2,4-oxadiazole-3-carboxylate (512). 

Tetrazole, l-methyl-5-phenyl-dipole moment, 5, 795 (80JHC1374)... 

Tetrazol-5-imine, 2-methyl-dipole moment, 5, 795 (56JA4197) Tetrazoline-5-thione, 1-phenyl- C NMR, 5, 805 (77JOC3725)... 

Chromone, 3-(tetrazol-5-yl)-antiallergic activity, 5, 836 degradation, 5, 815 Chromone, 3,5,7-trimethoxy-2-methyl-photolysis, 3, 695... 

UV spectra, 5, 798 synthesis, 5, 833 thermolysis, 5, 812 Tetrazole, 5-amino-2-methyl-methylation, 5, 818 Tetrazole, 2-aryl-5-substituted quatemization, 5, 815 Tetrazole, 5-aryl-acidity, 5, 816... 

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