An Efficient and Regioselective Synthesis of Tetrazoles under Transition - Metal Free Conditions
J. Environ. Nanotechnol., Volume 6, No 4 (2017) pp. 17-21
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.
Full Text
Reference
Academic, 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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
https://doi.org/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).
