ABSTRACT
Thiocarbamoylation reaction of 3-methyl-2-pyrazolin-5-one (1a) with two equivalents of PhNCS, resulted in the formation of 1,4-di(alpha-phenylthiocarbamoyl)-3-methylpyrazolone 3, which underwent cleavage of the thiocarbamoyl group at position 4 when coupled with aromatic diazonium salts affording 4-arylhydrazono-1-phenylthiocarbamoylpyrazolone (4a-j). Reactions of 4a with chloroacetyl chloride, benzenesulphonyl chloride, piperidine and hydrazine hydrate, resulted in the formation of 8.
Subject(s)
Pyrazoles/chemical synthesis , Indicators and Reagents , Magnetic Resonance Spectroscopy , Spectrophotometry, InfraredABSTRACT
Treatment of 2,3a,4,6,7a,8-hexahydrobenzo [1,2-c; 4,5-c] dipyrazole-3,7-dione (1) with chloroacetyl chloride gave the 2,6-bis (chloroacetyl) derivative (2), which on treatment with acetic anhydride pyridine afforded (3). Compound (2) when heated with pyridine afforded (1). Compound (1) underwent Mannich reaction with piperidine or morpholine and formaldehyde to give the 2,6-bis (piperidino or morpholinomethyl) derivatives (4a,b). Hydroxymethylation of (1) with formaldehyde gave the 2,6-bis (hydroxylmethyl) derivative (4), which on heating with piperidine afforded (4a), Reaction of 2,3a,4,6,7a,8-hexahydro- 2,6-bis (phenylsulphonyl) benzo [1,2-c; 4,5-c] dipyrazole-3,7-dione (7) with phenylmagnesium bromide gave dodecahydro-3,3,4a,7,7,8a-hexaphenyl-2,6- bis (phenylsulphonyl) benzo [1,2-c; 4,5-c] dipyrazole (8). Derivatives of hexahydrobenzodipyrazolone (9a-g) have been subjected to general screening for their antimicrobial activity.
Subject(s)
Anti-Bacterial Agents/chemical synthesis , Bacteria/drug effects , Pyrazoles/chemical synthesis , Acetylation , Alkylation , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Indicators and Reagents , Microbial Sensitivity Tests , Pyrazoles/chemistry , Pyrazoles/pharmacologySubject(s)
Anti-Infective Agents/chemical synthesis , Pyrimidinones/chemical synthesis , Thiazoles/chemical synthesis , Anti-Bacterial Agents , Anti-Infective Agents/pharmacology , Bacteria/drug effects , Escherichia coli/drug effects , Microbial Sensitivity Tests , Pyrimidinones/pharmacology , Saccharomyces cerevisiae/drug effects , Staphylococcus/drug effects , Staphylococcus aureus/drug effects , Thiazoles/pharmacologyABSTRACT
A new series of bispyrazolones were obtained upon treating the bishydrazone derivative 1 with dimethylsulphate, acetic anhydride, benzenesulphonyl chloride, piperidine, morpholine, N-methylaniline and formaldehyde respectively. A Mannich base was prepared from the interaction of 4-phenylhydrazone-3-methyl-2-pyrazolin-5-one and n-butylamine. The condensation of an N-hydroxy methyl derivative with ethyl acetoacetate and diethyl malonate led to the formation of the corresponding N-methyl derivatives. Some of the new bispyrazolones were screened to test their antimicrobial potentialities against Fusarium oxysporum fsp. hycopersici.
