A NOVEL SYNTHESIS OF 4-(5-SUBSTITUTED AMINOMETHYL)-1H-TETRAZOL-1-YL) BENZONITRILES
Keywords:
Acetoxyacetylchloride, Aminobenzonitrile, Trimethylsilylazide, TetrazoleAbstract
Objective: Synthesis of novel 4-(5-substituted amino methyl)-1H-tetrazol-1-yl)benzonitriles from p-aminobenzonitrile
Methods: A series of novel 4-(5-substituted amino methyl)-1H-tetrazol-1-yl)benzonitriles 6(a-f) were prepared starting from p-aminobenzonitrile 1which is protected with acetoxyacetylchloride, and followed by tetrazole formation with CH3SiN3 in DIAD/TPP conditions to form the 1-(4-cyanophenyl)-1H-tetrazol-5-yl) methyl acetate 3. This compound was hydrolyzed, followed by chlorination and treated with different amines to produce the title compounds.
Results: All structures of the newly synthesized compounds were confirmed by IR, NMR, mass spectral studies, and elemental analyses.
Conclusion: We developed a simple and efficient method for the preparation of 4-(5-substituted amino methyl)-1H-tetrazol-1-yl)benzonitriles form p-aminobenzonitrile through protection, tetrazole formation, hydrolysis, chlorination and amination as key steps with good yields and this method is highly useful for the synthesis of biologically potent highly substituted tetrazole derivatives.
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References
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