Journal of the Chemical Society C: Organic
Journal of the Chemical Society C: Organic was published between 1966 - 1971.
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Paper
J. Chem. Soc. C, 1971, 80 - 86, DOI: 10.1039/J39710000080
Mechanism of pyrazoline formation from the reactions of substituted hydrazines and Mannich bases
F. L. Scott, (Miss) S. A. Houlihan and D. F. Fenton
Aminoguanidinium nitrate reacts with Mannich bases, ArCO·CH2·CH2·NMe2 to form, depending upon the pH, di-
-keto-hydrazines, 1-amidino-
2-pyrazolines, or amidinohydrazone dinitrates. These substituted hydrazones do not display hydrazine anchimerism to form pyrazolines, probably because they exist in the wrong geometric form. The suggested mechanism for pyrazoline formation involves elimination from the Mannich base to form a vinyl ketone, which then forms a hydrazone (of the right configuration); subsequently this cyclises to the pyrazoline.
