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Molecules 2011, 16(1), 307-318; doi:10.3390/molecules16010307

Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus

1
Department of Chemistry, Faculty of Science, Jazan University, Jazan 2097, Saudi Arabia
2
Department of Biology, Faculty of Science, Jazan University, Jazan 2097, Saudi Arabia
3
Department of Chemistry, Faculty of Science, Al-Azhar University, Nasr City 11884, Cairo, Egypt
*
Author to whom correspondence should be addressed.
Received: 14 November 2010 / Revised: 14 December 2010 / Accepted: 15 December 2010 / Published: 5 January 2011
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Abstract

Vilsmeier formylation of 2-(1-phenylhydrazonoethyl)naphtho[2,1-b]furan (2) gave 3-naphtho[2,1-b]furan-2-yl-1-phenyl-1H-pyrazole-4-carbaldehyde (3), which was reacted with C- and N-nucleophiles to afford naphthofuranpyrazol derivatives 4-8. Treatment of 2-[(3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene]-malononitrile (4a) with reactants having active hydrogen and Et3N gave the corresponding pyrazoline, pyran and chromene addition product derivatives 10, 12 and 13, consisting of three different connected heterocyclic moieties. Reaction of 1-((3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl) methylene)-2-phenylhydrazone (6b) with AcONa and ethyl bromoacetate or chloroacetone afforded the thiazolidinone and methylthiazole derivatives 14 and 15, respectively. In addition, intramolecular cyclization of 6d with Ac2O afford the corresponding 1,3,4-thiadiazol-2-yl acetamide derivative 16. The structures of the synthesized compounds were confirmed by IR, 1H-NMR/13C-NMR and mass spectral studies. Compound 14 showed promising effects against the tested Gram positive and negative bacteria and fungi.
Keywords: Vilsmeier reaction; 2-[3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene]malononitrile; 1,3,4-thiadiazol-2-ylacetamide; antimicrobial activity Vilsmeier reaction; 2-[3-(naphtho[2,1-b]furan-2-yl)-1-phenyl-1H-pyrazol-4-yl)methylene]malononitrile; 1,3,4-thiadiazol-2-ylacetamide; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

El-Wahab, A.H.F.A.; Al-Fifi, Z.I.A.; Bedair, A.H.; Ali, F.M.; Halawa, A.H.A.; El-Agrody, A.M. Synthesis, Reactions and Biological Evaluation of Some New Naphtho[2,1-b]furan Derivatives Bearing a Pyrazole Nucleus. Molecules 2011, 16, 307-318.

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