Molecules 2012, 17(11), 13642-13655; doi:10.3390/molecules171113642
Article

Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material

1,* email, 1, 2,3 and 3,4
Received: 19 September 2012; in revised form: 9 November 2012 / Accepted: 12 November 2012 / Published: 19 November 2012
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: A series of pyridines, pyrimidinones, oxazinones and their derivatives were synthesized as antimicrobial agents using citrazinic acid (2,6-dihydroxyisonicotinic acid) as a starting material. α,β-Unsaturated ketones 3ac were condensed with cyanothio-acetamide in the presence of ammonium acetate to give 2-cyanopyridinethiones 4ac, which were reacted with ethyl chloroacetate to yield the corresponding cyano esters 5ac. The esters 5ac were cyclized by action of sodium methoxide to aminoesters 6ac, which were aminolyzed with ammonia to corresponding aminoamide derivatives 7a-c. Also, the esters 6ac were hydrolyzed with NaOH to the corresponding sodium salt 8ac, which were treated with acetic anhydride to afford 2-methyloxazinones 9ac. The latter compounds were treated with ammonium acetate to afford 2-methylpyrimidinones 10ac, followed by methylation with methyl iodide to yield 2,3-dimethyl-pyrimidinones 11ac. The antimicrobial screening showed that many of these compounds have good antibacterial and antifungal activities comparable to streptomycin and fusidic acid used as reference drugs.
Keywords: citrazinic acid; acryloyl candidates; oxazinone; pyrimidinone; antimicrobial agents
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MDPI and ACS Style

Hossan, A.S.M.; Abu-Melha, H.M.A.; Al-Omar, M.A.; Amr, A.E.-G. Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material. Molecules 2012, 17, 13642-13655.

AMA Style

Hossan ASM, Abu-Melha HMA, Al-Omar MA, Amr AE-G. Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material. Molecules. 2012; 17(11):13642-13655.

Chicago/Turabian Style

Hossan, Aisha S.M.; Abu-Melha, Hanaa M.A.; Al-Omar, Mohamed A.; Amr, Abd E.-G. 2012. "Synthesis and Antimicrobial Activity of Some New Pyrimidinone and Oxazinone Derivatives Fused with Thiophene Rings Using 2-Chloro-6-ethoxy-4-acetylpyridine as Starting Material." Molecules 17, no. 11: 13642-13655.

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