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

Nirmal T. Havannavar; L.V.G. Nargund; Lakshmi Narasu M.

Asian Journal of Research in Chemistry

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0974-4150 (Online)
0974-4169 (Print)

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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

Author(s): Nirmal T. Havannavar, L.V.G. Nargund, Lakshmi Narasu M.

Email(s): nirmal_th31@rediffmail.com

DOI: Not Available

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

Published In: Volume - 7, Issue - 10, Year - 2014

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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.

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Cite this article:
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.

Cite(Electronic):
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. Available on: https://ajrconline.org/AbstractView.aspx?PID=2014-7-10-8

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Asian Journal of Research in Chemistry

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

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