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Synthesis of Newly Substituted Pyrazoles and Substituted Pyrazolo[3,4‐ b ]Pyridines Based on 5‐Amino‐3‐Methyl‐1‐Phenylpyrazole
Author(s) -
ElEmary Talaat I.
Publication year - 2007
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200700072
Subject(s) - malononitrile , chemistry , acetophenone , hydrazine (antidepressant) , chloroacetyl chloride , semicarbazide , benzaldehyde , organic chemistry , medicinal chemistry , cyclohexanone , chloride , catalysis , chromatography
The reaction of the aminopyrazole 1 with benzenesulfonyl chloride, arenediazonium salt, chloroacetyl chloride, ethoxy methyleneamlononitrile and with ethyl 2‐cyano‐3‐ethoxyacrylate gave the substituted 3‐methyl‐1‐phenylpyrazole 2–5a,b . Compound 5b was cyclized to 6 and to 7 by treating it with AlCl 3 and with POCl 3 , respectively. Compound 6 converted to 7 by boiling it in POCl 3 /PCl 5 . Compound 10b was produced through reaction of 9 with acetophenone. Reaction of 1 with benzylidinemalononitrile afforded 11 . New methods for preparation of 15 and 16 are described. The reaction of 8 with malononitrile, thiosemicarbazide, phenyl hydrazine and acetophenone afforded compounds 18–21 . The reaction of 21 with malononitrile gave 22 . Compounds 23–26 were produced upon reaction of 10a with malononitrile, phenyl hydrazine, thiosemicarbazide, semicarbazide and with benzaldehyde, respectively.