Welcome to JENT its Thursday 18th of January 2018

Journal of Environmental Nanotechnology

(A Quarterly Peer-reviewed and Refereed International Journal)
ISSN(Print):2279-07 48; ISSN(Online):2319-5541
CODEN:JENOE2

An Efficient and Regioselective Synthesis of Tetrazoles under Transition - Metal Free Conditions

Abstract

A novel protocol for synthesisof series of tetrazoles is demonstrated via in-situformed secondary amides under transition-metal free conditions. The reaction well tolerates a wide variety of functional groups to afford structurally diverse tetrazoles in good to excellent yields at 70°C. All the synthesized compounds were characterized by FT- IR, 1H /13C NMR, LC-Mass spectral data and elemental analyses.

Article Type: Research Article

Corresponding Author: B. R. Venkatraman 2  

Email: brvenkatraman@yahoo.com

This article has not yet been cited.

K. Vijayakumar 1,  B. R. Venkatraman 2*.  

1, 2. Department of Chemistry, Periyar E.V.R. College (Autonomous), Tiruchirappalli, TN, India.

J. Environ. Nanotechnol., Volume 6, No. 4 pp. 17-21
ISSN: 2279-0748 eISSN: 2319-5541
ENT174289.pdf
Download Citation

Reference

Ademac, J., Waissser, K., Kunes, J. and Koustova, J., A note on the antitubercular activities of 1-aryl-5-benzylsulfanyltetrazoles, Arch. Pharm., 338(8), 385-389(2005).

doi:10.1002/ardp.200400967

Allen, F. H., Groom, C. R., Liebeschuetz, J. W., Bardwell, D. A., Olsson, T. S. G., Wood, P. A., The Hydrogen Bond Environments of 1H‐Tetrazole and Tetrazolate Rings: The Structural Basis for Tetrazole‐Carboxylic Acid Bioisosterism, J. Chem. Inf. Model., 52(3), 857-866(2012).

doi: 10.1021/ci200521k

Dai, L. L.,  Zhang, H. Z., Nagarajan, S.,  Rasheed, S.  and  Zhou, C. H., Synthesis of tetrazole compounds as a novel type of potential antimicrobial agents and their synergistic effects with clinical drugs and interactions with calf thymus DNA , Med. Chem. Commun., 6, 147-15(2015).

doi: 10.1039/C4MD00266K

Feinn, L., Dudley, J., Coca, A. and Roberts, E. L., Antimicrobial evaluation of 5-substituted aryl 1H-tetrazoles, Med. Chem., 13 (8), 359-364(2017).

doi:10.2174/1573406412666161220150028

Ikeda, T., Kakegawa, H., Miyataka, H., Matsumoto, H. and Satoh, T., Anti-allergic and anti-inflammatory actions of 2′-(tetrazole-5-yl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxanilide 1,1dioxide, Bioorg. Med. Chem. Lett., 2(7), 709-714(1992).

 doi: 10.1016/S0960-894X(00)80397-2

Imai, T., Harigae, R., Moriyama,  K. and Togo, H., ,Preparation of 5-aryl-2-alkyltetrazoles with aromatic aldehydes, alkylhydrazine, di-tert-butyl azodicarboxylate and bis(trifluoroacetoxy) iodo]benzene, J. Org. Chem., 81 (9), 3975-3980(2016).

doi: 10.1021/acs.joc.6b00606

Meanwell, N. A., Synopsis of some recent tactical application of bioisosteres in drug design, J. Med. Chem., 54(8), 2529‐2591(2011).

doi: 10.1021/jm1013693

Mohite, P. B., Pandhare, R. B., Khanage, S. G. and Bhaskar, V. H., Synthesis and antiinflammatory activity of 5-phenyl-1-(acyl)-1,2,3,4-tetrazole, J. Pharm. Res., 3(1), 43-46(2010).

Pagacz-Kostrzewa, M., Jesariew, D., Podruczna, M. and Wierzejewska, M., Infrared spectra and X-ray structure of (tetrazol-5-yl)acetic acid, Spectrochim. Acta. A Mol. Biomol. Spectrosc., 108, 229-235(2013).

doi: 10.1016/j.saa.2013.01.086

Shin-ichi, N., Taisei, U., Akito, N., Nobutoshi, M. and Jinsaku, S., Synthesis and central nervous system stimulant activity of camphor-1,2,4-triazines fused with 1,2,4-triazolo, tetrazolo and 1,2,4-triazine, Heterocycles, 44 (1), 117-120(1997).

doi : 10.3987/COM-96-S34

Varadaraji, D., Suban, S.S., Ramasamy, V. R., Kubendiran, K., Raguraman, J. K. G.,  Nalilu, S. K. and Pati, H. N., Synthesis and evaluation of a series of 1-substituted tetrazole derivatives as antimicrobial agents, Org. Commun., 3 (3),  45-56(2010).

>>