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Cross-linked poly (4-vinylpyridine) supported azide ion as a versatile and recyclable polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4-tetrazoles

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Abstract

Cross-linked poly (4-vinylpyridine) supported azide ion, [P4-VP]N3, is easily prepared and used as an efficient polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via condensation reaction of azide ion, primary aromatic amines, and triethyl orthoformate in glacial acetic acid. After optimization of the reaction conditions, a wide variety of primary aromatic amines were also subjected to preparation of the corresponding 1-aryl-1 H-1,2,3,4- tetrazoles using [P4-VP]N3 under heterogeneous conditions. In this method, the reaction times were very short and the isolated yields were excellent (90–98 %). 1-Aryl-1H-1,2,3,4- tetrazole products were characterized by Fourier transform infrared (FT-IR) and some of them were also characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, and physical properties were compared with the literature values of known compounds. The spent polymeric reagent were regenerated quantitatively and reused for several cycles without significant loss of their activity.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, Yazd University, P. O. Box 89195-74, Yazd, Iran

    Mohammad Ali Karimi Zarchi & Fatemeh Nazem

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  1. Mohammad Ali Karimi Zarchi
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  2. Fatemeh Nazem
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Correspondence to Mohammad Ali Karimi Zarchi.

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Karimi Zarchi, M.A., Nazem, F. Cross-linked poly (4-vinylpyridine) supported azide ion as a versatile and recyclable polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4-tetrazoles. J IRAN CHEM SOC 11, 91–99 (2014). https://doi.org/10.1007/s13738-013-0279-4

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  • DOI: https://doi.org/10.1007/s13738-013-0279-4

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