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Asian Journal of Research in Chemistry
Year : 2017, Volume : 10, Issue : 2
First page : ( 135) Last page : ( 141)
Print ISSN : 0974-4169. Online ISSN : 0974-4150.
Article DOI : 10.5958/0974-4150.2017.00022.0

Synthesis and antimicrobial evaluation of Azetidinone derivatives of pyridine containing hydrazides

Senwar Ram C.*, Rathore Krishna K., Mehta Anita

Department of Chemistry, M.L. Sukhadia University, Udaipur-313001, India

*Corresponding Author E-mail: ram.senwar09@gmail.com

Online published on 17 July, 2017.


Isoniazid (1a) undergoes facile condensation with indole-3-carboxaldehyde in methanolic media and glacial acetic acid as a catalyst to afford the corresponding N-((1H-indol-3-yl)methylene) nicotinohydrazide (2a). Cyclocondensation of compounds (2a) with chloro acetyl chloride, triethyl amine and 1, 4-dioxane yields N-(3-chloro-2-(1H-indol-3-yl)-4-oxoazetidin-1-yl)nicotinohydrazide (3a). Further the NH proton of indole in compounds (3a) is replaced with different benzo[b]thiophenes to yield the final compound N-(3-chloro-2-(1-(3-chlorobenzo[b]thiophene-2-carbonyl)-1H-indol-3-yl)-4-oxoazetidin-1-yl) nicotinohydrazide (4a-d). In an alternative reaction Nicotinic-hydrazide (1b) is used in place of Isoniazid and reacted with indole-3-carboxaldehyde to produce N-((1H-indol-3-yl)methylene) isonicotinohydrazide (2b). Compound (2b) on reaction with chloroacetylchloride, triethylamine and 1, 4-dioxane synthesize N-(3-chloro-2-(1H-indol-3-yl)-4-oxoazetidin-1-yl)isonicotinohydrazide (3b). In the final stage of the reaction scheme the NH proton of compound (3b) is replaced with different benzo[b]thiophenes to yield the final compounds N-(3-chloro-2-(1-(3-chloro benzo[b]thiophene-2-carbonyl)-1H-indol-3-yl)-4-oxoazetidin-1-yl)isonicotinohydrazide (4e-h). The structures of these compounds were established on the basis of analytical and spectral data. The newly synthesized compounds were evaluated for their antibacterial and antifungal activities.



Schiff base, Azetidinone, Benzo[b]thiophene, antibacterial and antifungal activity.


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