Journal :   Asian Journal of Research in Chemistry

Volume No. :   7

Issue No. :  10

Year :  2014

Pages :   882-887

ISSN Print :  0974-4169

ISSN Online :  0974-4150


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Synthesis and characterization of 2-(1-phenyl-5-aryl-4, 5-dihydro-3-pyrazolyl)-6-chloro-5-fluoro-3-phenylindoles and 2-(1-phenyl-5-aryl-3-pyrazolyl)-6-chloro-5-fluoro-3-phenylindoles



Address:   Nirmal T. Havannavar 1*, L.V.G. Nargund2 and Lakshmi Narasu M.3 1Department of Pharmaceutical Chemistry, M.M.U College of Pharmacy, Ramanagara-562159 Karnataka , India
2Department of Pharmaceutical Chemistry, Dattatreyanagar, BSK IIIrd Stage, Bangalore-560085, Karnataka, India
3Department of Biotechnology, IST, JNTU, Kukatpally, Hyderabad-500072
*Corresponding Author
DOI No:

ABSTRACT:
Phenyl hydrazone of 3-chloro-4-fluoro aniline 1 was obtained by coupling the diazonium chloride of chlorofluoro aniline with ethyl-a-benzyl acetoacetate in the presence of sodium acetate under the condition of modified Japp-Klingemann reaction. On passing hydrogen chloride gas for 1 hr the hydrazone underwent Fischer indole cyclization to give 2-acetyl-6-chloro-5-fluoro-3-phenylindole 2. It was then condensed with various aromatic aldehydes in the presence of sodium hydroxide in ethanol to get substituted chalcones 3a-g. Chalcones 3a-g were brominated to get dibromo chalcones 4a-g. Chalcones 3a-g were treated with phenyl hydrazine in presence of triethylamine to get title compounds 5a-g. Dibromo chalcones 4a-g were treated with phenyl hydrazine in triethanol amine to get title compounds 6a-g.
KEYWORDS:
2-acetyl-6-chloro-5-fluoro-3phenylindole, chalcones, phenyl hydrazine, pyrazolyl indoles.
Cite:
Nirmal T. Havannavar, L.V.G. Nargund, Lakshmi Narasu M.. Synthesis and characterization of 2-(1-phenyl-5-aryl-4, 5-dihydro-3-pyrazolyl)-6-chloro-5-fluoro-3-phenylindoles and 2-(1-phenyl-5-aryl-3-pyrazolyl)-6-chloro-5-fluoro-3-phenylindoles. Asian J. Research Chem. 7(10): October- 2014; Page 882-887.
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