Author/Authors :
Yogi, Prabhunath Synthetic Organic Chemistry Laboratory - Department of Chemistry - Mewar University, Gangrar, Rajasthan, India , Ashid, Mohammad Synthetic Organic Chemistry Laboratory - Department of Chemistry - Mewar University, Gangrar, Rajasthan, India , Hussain, Nasir Department of Chemistry - Vidya Bhawan Rural Institute, Udaipur (Raj.), India. , Khanam, Rehana Department of Chemistry - Vidya Bhawan Rural Institute, Udaipur (Raj.), India , Khan, Saba Department of Chemistry - Vidya Bhawan Rural Institute, Udaipur (Raj.), India , Joshi, Ajit Synthetic Organic Chemistry Laboratory - Department of Chemistry - Mewar University, Gangrar, Rajasthan, India
Abstract :
Phenyl hydrazine treated with variable acetophenone to give substituted phenyl carbonyl hydrazone compounds, 1-(1-substituted -2-ylethylidene)-2-phenylhydrazine (1a-e). This is undergoing cyclization by using Vilsmeier-Haack reaction and afforded compounds 3-substituted-2-yl-1-phenyl-1H-pyrazole-4-carbaldehyde (2a-e). The reaction of an N,N disubstituted formamide, such as DMF or N-methylformanilide, with acid chlorides, such as phosphoryl chloride or phosgene, leads to the formation of an adduct, this adduct usually referred to as a Vilsmeier Haack reagent. In one path compound 2a-e reflux with pyrazolone and give compound 4-[(3-substituted -2-yl-1-phenyl-1H-pyrazol-4-yl)methylidene]-5-methyl-2,4-dihydro-3H-pyrazol-3-one (3a-e), in another pathway compounds 2(a-e) react with thiazolidione and give target molecule compounds 5-{[3-(4-substitutedphenyl)-1-phenyl-1H-pyrazol-4-yl]methylidene}-1,3-thiazolidine-2,4-dione (4a-e). The structures of all the synthesized compounds were supported by spectral and analytical studies.
Keywords :
Vielsmeier-Haack reaction , Phenyl hydrazine , Substituted Acetophenone , Pyrazolone , Thiazolidione , Spectral data
