The base-promoted reactions of easily accessible α-aminohydrazones represent a simple and efficient method for the preparation of both 1-substituted and 1-unsubstituted-4-aminocarbonyl-1H-pyrazol-5(2H)-ones, whereas the copper promoted reactions provide a divergent facile regiocontrolled synthesis of the imidazoline/imidazole ring system. The copper-promoted reaction of the α-benzylaminohydrazone produces a 2-oxo-1,4-diazadiene derivative. Finally, the imidazolines can be easily hydrolyzed to α-ketohydrazones.
Synthesis of functionalised pyrazolones and imidazolines/imidazoles through divergent cyclization reactions / G. Abbiati, A. Arcadi, O.A. Attanasi, L. De Crescentini, E. Rossi. - In: TETRAHEDRON. - ISSN 0040-4020. - 57:10(2001 Mar 13), pp. 2031-2038.
Synthesis of functionalised pyrazolones and imidazolines/imidazoles through divergent cyclization reactions
G. AbbiatiPrimo
;E. RossiUltimo
2001
Abstract
The base-promoted reactions of easily accessible α-aminohydrazones represent a simple and efficient method for the preparation of both 1-substituted and 1-unsubstituted-4-aminocarbonyl-1H-pyrazol-5(2H)-ones, whereas the copper promoted reactions provide a divergent facile regiocontrolled synthesis of the imidazoline/imidazole ring system. The copper-promoted reaction of the α-benzylaminohydrazone produces a 2-oxo-1,4-diazadiene derivative. Finally, the imidazolines can be easily hydrolyzed to α-ketohydrazones.
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