Cyclic and acyclic products from the reactions between methyl 3-oxobutanoate and arylhydrazines.
The molecules of methyl 3-(2-nitrophenylhydrazono)butanoate, C(11)H(13)N(3)O(4), (I), and methyl 3-(2,4-dinitrophenylhydrazono)butanoate, C(11)H(12)N(4)O(6), (II), both prepared from methyl 3-oxobutanoate and the corresponding nitrophenylhydrazine, exhibit polarized molecular electronic structures; in each of (I) and (II), the molecules are linked into chains by a single C-H...O hydrogen bond. The molecules of 5-hydroxy-3-methyl-1-phenyl-1H-pyrazole, C(10)H(10)N(2)O, (III), prepared by the reaction of methyl 3-oxobutanoate and phenylhydrazine, are linked into chains by a single O-H...N hydrogen bond. The reaction between methyl 3-oxobutanoate and 3-nitrophenylhydrazine yields 5-hydroxy-3-methyl-1-(3-nitrophenyl)-1H-pyrazole, (IV), which when crystallized from acetone yields 4-isopropylidene-3-methyl-1-(3-nitrophenyl)-1H-pyrazol-5(4H)-one, C(13)H(13)N(3)O(3), (V).
Wardell
James L
JL
Instituto de Química, Departamento de Química Inorgânica, Universidade Federal do Rio de Janeiro, 21945-970 Rio de Janeiro, RJ, Brazil.
Skakle
Janet M S
JM
Low
John N
JN
Glidewell
Christopher
C