Abstract

The title compounds are five-membered heterocycles having two adjacent nitrogen atoms within the ring. Pyrazoles have two endocyclic bonds and possess aromatic and tautomeric properties. Pyrazolones also have two double bonds, one of which is attached to an exocyclic oxygen atom. Pyrazolines have only one endocyclic double bond. The structural elucidation of pyrazoles and derivatives has been greatly aided by nuclear magnetic resonance spectroscopy, especially for distinguishing between isomeric structures. Pyrazoles are stable compounds and their boiling points increase with an increase in the number of alkyl groups on carbon; solubility in organic solvents is also increased. Substitution on nitrogen decreases the boiling point because of the elimination of hydrogen bonding. Pyrazolines are usually liquids having high boiling points and low water solubility, and are basic in nature. Pyrazolones are often crystalline solids and their characteristics are strongly influenced by the predominant tautomeric form. Pyrazoles can react with both acids and bases, and can be halogenated, nitrated, and acylated on both N and C. Pyrazolines are much less stable, resulting in facile ring opening. Pyrazolones react with diazonium salts, an important process in the dye industry. The preferred synthetic method for the title compounds utilizes the reaction of hydrazines with bifunctional compounds, such as -diketones and esters, and -keto acetylenic compounds. In an alternative procedure, diazo compounds replace hydrazines and ring formation takes place via 1,3-dipolar cycloaddition. Pyrazoles and pyrazolones are widely used in the pharmaceutical industry to alleviate inflammation, fever, pain, and infections. To a lesser extent, they are also used as insecticides and herbicides. Pyrazolones linked to azo compounds are extensively used in the dye industry; some pyrazolines display insecticidal activity.