Abstract
By treating 5-aminotetrazole with aromatic α,β-unsaturated ketones or with Mannich base hydrochlorides there have been synthesized aromatic substituted 4,7-dihydrotetrazolo[1,5-a]-pyrimidines. They can be reduced to the corresponding 4,5,6,7-tetrahydro derivatives by the action of NaBH4. The high thermodynamic stability of the 4,7-dihydrotetrazolo[1,5-a]pyrimidines when compared with the 4,5-dihydro isomers has been revealed. Reaction of 5-aminotetrazole both with cyclohexanone as well as with 2-cyclohexylidenecyclohexanone leads to formation of 9,9-pentamethylene-4,5,6,7,8,9-hexahydrotetrazolo[5,1-b]quinazoline, the structure of which was demonstrated using X-ray crystallography.
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Desenko, S.M., Gladkov, E.S., Komykhov, S.A. et al. Partially Hydrogenated Aromatic Substituted Tetrazolo[1,5-a]pyrimidines. Chemistry of Heterocyclic Compounds 37, 747–754 (2001). https://doi.org/10.1023/A:1011925631511
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DOI: https://doi.org/10.1023/A:1011925631511