A NOVEL SYNTHESIS OF 4-(5-SUBSTITUTED AMINOMETHYL)-1H-TETRAZOL-1-YL) BENZONITRILES


K. Venkatanarsimha Rao, Boina Gopal Rao, Bethanamudi Prasanna

Abstract


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.

 


Keywords


Acetoxyacetylchloride, Aminobenzonitrile, Trimethylsilylazide, Tetrazole.

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About this article

Title

A NOVEL SYNTHESIS OF 4-(5-SUBSTITUTED AMINOMETHYL)-1H-TETRAZOL-1-YL) BENZONITRILES

Keywords

Acetoxyacetylchloride, Aminobenzonitrile, Trimethylsilylazide, Tetrazole.

Date

04-11-2014

Additional Links

Manuscript Submission

Journal

International Journal of Pharmacy and Pharmaceutical Sciences
Vol 6, Issue 11, 2014 Page: 393-395

Online ISSN

0975-1491

Statistics

186 Views | 36 Downloads

Authors & Affiliations

K. Venkatanarsimha Rao
R&D Bharatiyar University
India

Boina Gopal Rao
Chaitanya Post Graduate College (Autonomous), Hanamkonda
India

Bethanamudi Prasanna
Chaitanya Post Graduate College(Autonomous) Hanamkonda Warangal
India


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