Synthesis of Novel 2-Alkyl-5-{4-[(3-alkylisoxazol-5-yl)methoxy]phenyl}-2H-tetrazoles
Yousef Rastgar Mirzaei,1,* Samad Bavili Tabrizi2 and Laden Edjlali2
1 Organic Synthesis Laboratory, Faculty of Chemistry,
University of Tabriz, Tabriz 51664, Iran
2 Department of Applied Chemistry, Faculty of Science, Islamic Azad
University-Tabriz, P. O. Box 1655 Tabriz, Iran
* Corresponding author: E-mail: mirzaeyr@uwec.edu;
mirzaeiyousef@yahoo.com Fax: +(715)
836-4979
Dedicated to Prof. Dr. Nicholas R. Natale on the occasion of his 57th birthday.
Abstract
Several alkyl(isoxazolylmethoxyphenyl)tetrazoles were synthesized and
characterized. 3-Alkyl-5-(chloromethyl)isoxazoles 9 were prepared by the
reaction of corresponding (3-alkylisoxazol-5-yl)methanols with thionyl chloride.
4-(2-Alkyl-2H-tetrazol-5-yl)phenols 8 were synthesized from the
corresponding aldehyde 3 in five steps, which then reacted with 3-alkyl-5-(chloromethyl)isoxazoles
9 to produce the corresponding 2-alkyl-5-{4-[(3-alkylisoxazol-5-yl)methoxy]
phenyl}-2H-tetrazoles 10a–h in high yields.
Keywords: Cycloaddition, Isoxazole, Nitro compounds, Tetrazole.