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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

Rapid Cesium Fluoride Catalyzed Synthesis of 5-Aryloxy-1-phenyl-1Htetrazoles via Nucleophilic Aromatic Substitution

Author(s): Khalid Mohammed Khan*, Itrat Fatima, Shahnaz Perveen and Syed Muhammad Saad

Volume 18, Issue 5, 2021

Published on: 28 July, 2020

Page: [389 - 394] Pages: 6

DOI: 10.2174/1570178617999200728211046

Price: $65

Abstract

A nucleophilic aromatic substitution via a new and facile cesium fluoride catalyzed synthetic approach to get 5-aryloxy-1-phenyl-1H-tetrazoles was developed. Dual usage of cesium fluoride as a nucleophilic catalyst as well as an electrophilic catalyst afforded the desired products at room temperature in a short reaction time without purification in high yields. This simple but useful reaction may be a rapid and reliable strategy for the synthesis of tetrazolyl ethers.

Keywords: Tetrazole, diaryl ether, nucleophilic aromatic substitution, cesium fluoride, catalysis, methodology.

Graphical Abstract
[1]
Roh, J.; Vávrová, K.; Hrabálek, A. Eur. J. Org. Chem., 2012, 6101-6118.
[http://dx.doi.org/10.1002/ejoc.201200469]
[2]
Dai, L.L.; Zhang, H.Z.; Nagarajan, S.; Rasheed, S.; Zhou, C.H. MedChemComm, 2015, 6, 147-154.
[http://dx.doi.org/10.1039/C4MD00266K]
[3]
Faria, J.V.; dos Santos, M.S.; Bernardino, A.M.; Becker, K.M.; Machado, G.M.; Rodrigues, R.F.; Canto-Cavalheiro, M.M.; Leon, L.L. Bioorg. Med. Chem. Lett., 2013, 23(23), 6310-6312.
[http://dx.doi.org/10.1016/j.bmcl.2013.09.062] [PMID: 24125880]
[4]
Bhalla, Y.; Puri, E.; Monga, P.; Sapra, S. iP-Planet, 2013, 1, 20-30.
[5]
Pais, G.C.; Zhang, X.; Marchand, C.; Neamati, N.; Cowansage, K.; Svarovskaia, E.S.; Pathak, V.K.; Tang, Y.; Nicklaus, M.; Pommier, Y.; Burke, T.R., Jr J. Med. Chem., 2002, 45(15), 3184-3194.
[http://dx.doi.org/10.1021/jm020037p] [PMID: 12109903]
[6]
Momose, Y.; Maekawa, T.; Odaka, H.; Ikeda, H.; Sohda, T. Chem. Pharm. Bull. (Tokyo), 2002, 50(1), 100-111.
[http://dx.doi.org/10.1248/cpb.50.100] [PMID: 11824568]
[7]
Costantino, G.; Maltoni, K.; Marinozzi, M.; Camaioni, E.; Prezeau, L.; Pin, J-P.; Pellicciari, R. Bioorg. Med. Chem., 2001, 9(2), 221-227.
[http://dx.doi.org/10.1016/S0968-0896(00)00270-4] [PMID: 11249114]
[8]
Lei, G.; Xiong, X.; Wei, Y.; Zheng, X.; Zheng, J. J.; Chromatogr, A 2008, 1187(1-2), 197-204.
[http://dx.doi.org/10.1016/j.chroma.2008.02.031] [PMID: 18313064]
[9]
Wang, S-H.; Zheng, F-K.; Zhang, M-J.; Liu, Z-F.; Chen, J.; Xiao, Y.; Wu, A-Q.; Guo, G-C.; Huang, J-S. Inorg. Chem., 2013, 52(17), 10096-10104.
[http://dx.doi.org/10.1021/ic401409b] [PMID: 23937409]
[10]
Wu, F-T.; Liu, P.; Ma, X-W.; Xie, J-W.; Dai, B. Chin. Chem. Lett., 2013, 24, 893-896.
[http://dx.doi.org/10.1016/j.cclet.2013.05.037]
[11]
Khan, K.M.; Fatima, I.; Saad, S.M.; Taha, M.; Voelter, W. Tetrahedron Lett., 2015, 57, 523-524.
[http://dx.doi.org/10.1016/j.tetlet.2015.12.067]
[12]
Galli, C. Org. Prep. Proced. Int., 1992, 24, 285-307.
[http://dx.doi.org/10.1080/00304949209355891]
[13]
Xie, L.Y.; Qu, J.; Peng, S.; Liu, K.J.; Wang, Z.; Ding, M.H.; Wang, Y.; Cao, Z.; He, W.M. Green Chem., 2018, 20, 760-764.
[http://dx.doi.org/10.1039/C7GC03106H]
[14]
Clark, J.H. Chem. Rev., 1980, 80, 429-452.
[http://dx.doi.org/10.1021/cr60327a004]
[15]
Singh, R.P.; Cao, G.; Kirchmeier, R.L.; Shreeve, J.M. J. Org. Chem., 1999, 64(8), 2873-2876.
[http://dx.doi.org/10.1021/jo982494c] [PMID: 11674359]
[16]
Kim, D.W.; Jeong, H-J.; Lim, S.T.; Sohn, M-H.; Katzenellenbogen, J.A.; Chi, D.Y. J. Org. Chem., 2008, 73(3), 957-962.
[http://dx.doi.org/10.1021/jo7021229] [PMID: 18166063]
[17]
Mee, S.P.; Lee, V.; Baldwin, J.E. Chemistry, 2005, 11(11), 3294-3308.
[http://dx.doi.org/10.1002/chem.200401162] [PMID: 15786503]
[18]
Poon, P.S.; Bedoya, L.; Churio, G.J.; Banerjee, A.K. Nat. Prod. Res., 2014, 28(20), 1747-1753.
[http://dx.doi.org/10.1080/14786419.2014.945171] [PMID: 25111320]
[19]
Nicolas, E.; Dharanipragada, R.; Toth, G.; Hruby, V.J. Tetrahedron Lett., 1989, 30, 6845-6848.
[http://dx.doi.org/10.1016/S0040-4039(01)93367-2]
[20]
Schuster, D.; Spetea, M.; Music, M.; Rief, S.; Fink, M.; Kirchmair, J.; Schütz, J.; Wolber, G.; Langer, T.; Stuppner, H.; Schmidhammer, H.; Rollinger, J.M. Bioorg. Med. Chem., 2010, 18(14), 5071-5080.
[http://dx.doi.org/10.1016/j.bmc.2010.05.071] [PMID: 20580236]
[21]
Hayat, S.; Choudhary, M.I.; Khan, K.M.; Schumann, W.; Bayer, E. Tetrahedron, 2001, 57, 9951-9957.
[http://dx.doi.org/10.1016/S0040-4020(01)00989-9]
[22]
Shah, S.T.A.; Khan, K.M.; Heinrich, A.M.; Choudhary, M.I.; Voelter, W. Tetrahedron Lett., 2002, 43, 8603-8606.
[http://dx.doi.org/10.1016/S0040-4039(02)02060-9]
[23]
Shah, S.T.A.; Khan, K.M.; Heinrich, A.M.; Voelter, W. Tetrahedron Lett., 2002, 43, 8281-8283.
[http://dx.doi.org/10.1016/S0040-4039(02)02028-2]
[24]
Shah, S.T.A.; Khan, K.M.; Fecker, M.; Voelter, W. Tetrahedron Lett., 2003, 44, 6789-6791.
[http://dx.doi.org/10.1016/S0040-4039(03)01402-3]
[25]
Shah, S.T.; Khan, K.M.; Hussain, H.; Hayat, S.; Voelter, W. Monatsh. Chem., 2005, 136, 1583-1589.
[http://dx.doi.org/10.1007/s00706-005-0351-6]
[26]
Khan, K.M.; Hayat, S. Synth. Commun., 2003, 33, 3435-3453.
[27]
Shah, S.T.A.; Khan, K.M.; Hussain, H.; Anwar, M.U.; Fecker, M.; Voelter, W. Tetrahedron, 2005, 61, 6652-6656.
[http://dx.doi.org/10.1016/j.tet.2005.03.126]
[28]
Khan, K.M.; Khan, I.; Perveen, S.; Malik, M.I. J. Fluor. Chem., 2014, 158, 1-5.
[http://dx.doi.org/10.1016/j.jfluchem.2013.11.010]
[29]
Hussey, B.J.; Johnstone, R.A.; Entwistle, J.D. Tetrahedron, 1982, 38, 3775-3781.
[http://dx.doi.org/10.1016/0040-4020(82)80091-4]
[30]
Bethell, D.; Johnstone, R.A.; Price, P.J. J. Chem. Soc. Chem. Commun., 1985, 5, 303-304.
[http://dx.doi.org/10.1039/c39850000303]
[31]
Akbulut, U.; Toppare, L.; Utley, J.H. J. Chem. Soc., Perkin Trans. 2, 1982, 4, 391-394.
[http://dx.doi.org/10.1039/P29820000391]
[32]
Johnstone, R.A.; Price, P.J. J. Chem. Soc., Perkin Trans. 1, 1987, 1069-1076.
[http://dx.doi.org/10.1039/p19870001069]
[33]
Goldfarb, D.S. US Patent US20090163545 A, 2009, 1, 25.

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