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Ring contraction of a 3-hydroxy-1-pyrazoline Derivative to a cyclopropanol derivative

✍ Scribed by Philip L. Southwick; Nazih Latif; James E. Klijanowicz; John G. O'Connor

Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
192 KB
Volume
11
Category
Article
ISSN
0040-4039

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✦ Synopsis

The reoent publication of several aomwnicationa regarding the preparation and properties of a 3-hydroxy-l-pyraaoline (1) and other qrclic and acyclic o-bydroxyalkyldiazenes (2) prompts us to report the preparation of a new group of compounds (V) containing a 3-hydroxy-1-pgmsolne structure which, unlike the 3-hydroxy-1-pgmzollne previously described, readily lose nitrogen with ring contmation to yield products (VII) incorporating a cyclopropanol structure.

Hydrazine reacted at 0' in ethanol with 4-benzylidene-2,3_dioxopyrrolidines (I) to yield adducts to which the S-substituted-6z-hyd~-6-oxo-~aryloctabydropyrrolo~3,4-c] pyrazole structure (II) has been assigned. These compounds appear to be the first in which a 3-hydroxrpymzolidine structure has been sufficiently stable to penzit characterization. Spectroscopic and analytical data were oonsistent only with structure II wng the reasonable possibilities for these bdrazine adducts; their ultraviolet spectra showed only the absorption of an a-l-substituted phenyl group, the infrared spectra indicated the Presence of NH and/or OH groups but the absance of a ketonic carbonyl, and the n.m.r. spectra revealed the presence of the system of four coupled protons represented by Aa, IEJ, UC and Hd in

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