Abstract
2-Methyl-4-hydrazinoquinazoline is shown to give on diazotization a covalent hydration product, 5, 5-dihydro-5-methyl-5-hydroxytetrazolo [1, 5-c]quinazoline (V). 2-phenyl-4-hydrazino-quinazoline gives the nonhydrated 5-phenyltetrazolo [1, 5-c]-quinazoline (IIb). Hydrolysis of the hydrated 5-methyl derivative V is shown to result in opening of the pyrimidine ring and formation of 5-(2′-aminophenyl)tetrazole, while hydrolysis of the 5-phenyl derivative IIb is found to give, via the azide, 2-phenylquinazoline. Possible reasons for the different behavior on hydrolysis are considered.
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