592553-00-9Relevant academic research and scientific papers
Reactions of 4-aryl-2-hydrazino-3-nitro-6-R-quinolines with HNO2
Grishchuk,Ivanov,Kuz'min,Turyanskaya,Ivanova
, p. 340 - 343 (2003)
The reaction of 4-aryl-2-hydrazino-3-nitro-6-R-quinolines with NaNO2 in AcOH gives the corresponding tetrazolo[1,5-a]quinolines. In contrast to tetrazolo[1,5-c]pyrimidines they cannot be converted to 6-R-4-phenyl[1,2,5]oxadiazolo[3,4-b]quinoline-3-oxides by heating in THF, toluene, or AcOH. Total energy quantum-chemical calculations using the MTNDO/3 and MNDO methods show that [1,2,5]oxadiazolo[3,4-b]quinoline-3-oxides are significantly higher in energy (230-280 kcal/mol) than the mentioned tetrazolo[1, 5-a]quinolines and hence their formation is unlikely.
