Abstract
Reaction of isatin with acetophenone derivatives gave 3‐hydroxy‐3‐phenacyl oxindole derivatives (II), dehydration of (II) gave 3‐phenacylidene‐2‐indolinone derivatives (III). Condensation of (III) with hydrazine hydrate, phenylhydrazine and phenylthiourea afforded new spiropyrazolines (IV & V) and spiropyrimidinethione (VI) respectively. The structures of the final products were established by physical and spectral means.
Highlights
The reaction of isatin with various compounds have been under intensive studies by many authors[1,2,3,4,5,6] and due to the importance of some derivatives, for example, pyrazoline and pyrimidinethione in different biological and industrial aspects[7,8], this research work has been initiated to prepare such new molecules
A mixture of 0.01 mole of compound (IIa-c), ethanol 25 mL and 50 mL of dilute HCl solution (25%), was allowed to stand overnight, fine orange needles were formed
The precipitate formed after concentration was filtered and washed with cold ethanol and recrystallised from acetic acid
Summary
The reaction of isatin with various compounds have been under intensive studies by many authors[1,2,3,4,5,6] and due to the importance of some derivatives, for example, pyrazoline and pyrimidinethione in different biological and industrial aspects[7,8], this research work has been initiated to prepare such new molecules. The reaction of isatin with acetophenone derivatives (Ia-c ) was carried out in the presence of diethyl amine as a basic catalyst giving rise to 3-hydroxy-3-phenacyl oxindoles (IIa-c) in good yields. Dehydration of the above compounds by dilute alcoholic hydrochloric acid gave 3-phenacylidene-2-indolinones (IIIa-c) in quantitative yields. The reaction of compound (III) with hydrazine, phenylhydrazine were carried out in presence of diethyl amine and gave spiropyrazoline (IV) and spiro-N-phenylpyrazoline (V) respectively.
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