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Int. J. Mol. Sci. 2013, 14(2), 2967-2979; doi:10.3390/ijms14022967
Article

Synthesis and Antimicrobial Evaluation of Some Novel Bis-α,β-Unsaturated Ketones, Nicotinonitrile, 1,2-Dihydropyridine-3-carbonitrile, Fused Thieno[2,3-b]pyridine and Pyrazolo[3,4-b]pyridine Derivatives

Department of Measurements and Environmental Applications, National Institute of Laser Enhanced Sciences (NILES), Cairo University, Giza 12613, Egypt
Received: 27 November 2012 / Revised: 9 January 2013 / Accepted: 10 January 2013 / Published: 30 January 2013
(This article belongs to the Section Material Sciences and Nanotechnology)
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Abstract

The title compounds were prepared by reaction of 1,1'-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)diethanone (1) with different aromatic aldehydes 2ac, namely Furfural (2a), 4-chlorobenzaldehyde (2b) and 4-methoxybenzaldhyde (2c) to yield the corresponding α,β-unsaturated ketones 3ac. Compound 3 was reacted with malononitrile, 2-cyanoacetamide or 2-cyanothioacetamide yielded the corresponding bis[2-amino-6-(aryl)nicotinonitrile] 4ac, bis[6-(2-aryl)-2-oxo-1,2-dihydropyridine-3-carbonitrile] 5ac or bis[6-(2-aryl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile] 6a,b, respectively. The reaction of compound 6a with each of 2-chloro-N-(4-bromophenyl) acetamide (7a), chloroacetamide (7b) in ethanolic sodium ethoxide solution at room temperature to give the corresponding 4,4'-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis-6-(2-furyl)thieno[2,3-b]pyridine-2-carboxamide] derivatives 9a,b. While compound 6a reacted with hydrazine hydrate yielded the 4,4'-(5-methyl-1-phenyl-1H-pyrazole-3,4-diyl)bis[6-(2-furyl)-1H-pyrazolo[3,4-b]pyridin-3-amine] 11. The structures of the products were elucidated based on their spectral properties, elemental analyses and, wherever possible, by alternate synthesis. Antimicrobial evaluation of the products was carried out.
Keywords: heterocycles; α,β-unsaturated ketones; pyrazoles; antimicrobial activity heterocycles; α,β-unsaturated ketones; pyrazoles; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Altalbawy, F.M.A. Synthesis and Antimicrobial Evaluation of Some Novel Bis-α,β-Unsaturated Ketones, Nicotinonitrile, 1,2-Dihydropyridine-3-carbonitrile, Fused Thieno[2,3-b]pyridine and Pyrazolo[3,4-b]pyridine Derivatives. Int. J. Mol. Sci. 2013, 14, 2967-2979.

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