J. Iran. Chem. Soc., Vol. 7, No. 3 September 2010, pp.685~694.

Current location: JICS Archive > Vol. 7 > No. 3 > Articles : 17

Synthesis and Characterization of 2-Alkyl -5-{4-[(3-nitrophenyl-5-isoxazolyl)methoxy]phenyl}-2H-tetrazoles

              Y.R. Mirzaeia,* and L. Edjlalib

aDepartment of Chemistry, University of Wisconsin-Eau Claire,Eau Claire, WI 54702, USA
        bDepartment of Applied Chemistry, Faculty of Science, Islamic Azad University-Tabriz Branch, P. O. Box 1655 Tabriz, Iran

Heteroaryl substituted analogs of antirhnoviral (A), was prepared by a convergent approach. 3-Nitrophenyl-5-bromooromethylisoxazoles 5a-b were synthesized by [3+2] cycloaddition of 3-(benzoyloxy)-propyne 2 to in situ generated arylnitrile oxides followed by deprotection of cycloadducts 3a-b and bromination of the resulting alcohols 4a-b. Coupling of 3-nitrophenyl-5-bromooromethylisoxazoles (5a-b) with 4-[5-(2-alkyl-2H-tetrazolyl)]phenols (6a-d) in N-methylpyrrolidinone under mild conditions afforded a new series of 2-alkyl-5-{4-[1-(3-nitrophenyl-5-isoxazolyl)methyloxy]phenyl}-2H-tetrazoles (7a-h) in high yields. The structures of the synthesized compounds were confirmed by their 1H NMR, Mass spectral, and Elemental Analysis data.

Keywords: Isoxazolyl-Tetrazolyl ethers, [3+2] Cycloaddition, Isoxazole, Nitro compounds, Tetrazole

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