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Synthesis of Triazenes of N-Heterocycles Mediated by Resin Immobilized Diazonium Ions
Corresponding Author(s) : Pranab J. Das
Asian Journal of Chemistry,
Vol. 29 No. 5 (2017): Vol 29 Issue 5
Abstract
Diazonium ions were prepared from aromatic amines and immobilized in cation exchange resin support and used for the synthesis of triazenes of piperidine and morpholine in a solid phase synthesis. Immobilization is an excellent technique for the stabilization of diazonium ions and can be preserved in the solid state. Using resin immobilized diazonium ions, triazene synthesis is carried out in the absence of acids thereby increasing the yield of the product and simplifying work up.
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- R. Lazny, J. Poplawski, J. Kobberling, D. Enders and S. Bräse, Synlett, 1304 (1999); https://doi.org/10.1055/s-1999-2803.
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- P. Scott, Linker Synthesis in Solid Phase Organic Synthesis, Wiley–VCH, Weinheim (2009).
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References
J. Hollaender, W.P. Neumann and G. Alester, Chem. Ber., 105, 1540 (1972); https://doi.org/10.1002/cber.19721050510.
J. Stawinski, T. Hozumi and S.A. Narang, Can. J. Chem., 54, 670 (1976); https://doi.org/10.1139/v76-096.
M. Julliard, G. Vernin and J. Metzger, Helv. Chim. Acta, 63, 467 (1980); https://doi.org/10.1002/hlca.19800630217.
B.H. Venger, C. Hansch, G.J. Hatheway and Y.U. Amrein, J. Med. Chem., 22, 473 (1979); https://doi.org/10.1021/jm00191a003.
M.L. Gross, D.H. Blank and W.M. Welch, J. Org. Chem., 58, 2104 (1993); https://doi.org/10.1021/jo00060a028.
R. Lazny, J. Poplawski, J. Kobberling, D. Enders and S. Bräse, Synlett, 1304 (1999); https://doi.org/10.1055/s-1999-2803.
R. Lazny, M. Sienkiewicz and S. Brase, Tetrahedron, 57, 5825 (2001); https://doi.org/10.1016/S0040-4020(01)00495-1.
S. Brase, S. Dahmen and M. Pfefferkorn, J. Comb. Chem., 2, 710 (2000); https://doi.org/10.1021/cc000051s.
K.H. Gordon and S. Balasubramanian, Org. Lett., 3, 53 (2001); https://doi.org/10.1021/ol006766l.
D. Enders, C. Rijksen, E. Bremus-Köbberling, A. Gillner and J. Köbberling, Tetrahedron Lett., 45, 2839 (2004); https://doi.org/10.1016/j.tetlet.2004.02.002.
L. Zaijun, Z. Qiying and P. Jiaomai, Rev. Anal. Chem., 22, 91 (2003).
B. Chen, A.K. Flatt, H. Jian, J.L. Hudson and J.M. Tour, Chem. Mater., 10, 1 (2005).
T. Giraldi, T.A. Conners and G. Carter, Triazenes-Chemical, Biological and Clinical Aspects, Plenum Press, New York (1990).
K.L. Kirk, J. Org. Chem., 43, 4381 (1978); https://doi.org/10.1021/jo00416a033.
K. Vaughan and K.F.G. Stevens, Chem Soc. Rev. B, 7, 377 (1978); https://doi.org/10.1039/cs9780700377.
A. Dorababu, R. Kamble, H. Devarajegegowda and G.Y. Meti, Org. Chem. Lett., 2, 12 (2015).
G.A. Smirnov, P.B. Gordeev, S.V. Nikitin, G.V. Pokhvisneva, T.V. Ternikova and O.A. Lukyanov, Russ. Chem. Bull., 64, 1057 (2015); https://doi.org/10.1007/s11172-015-0976-5.
B.S. Furniss, P.W. Hannaford and A.R. Tatchell, Vogel’s Textbook of Practical Organic Chemistry, Pearson Education, edn 5 (2008).
P. Scott, Linker Synthesis in Solid Phase Organic Synthesis, Wiley–VCH, Weinheim (2009).
A. Zarei, L. Khazdooz, H. Aghaei, G. Azizi, A.N. Chermahini and A.R. Hajipour, Dyes Pigments, 101, 295 (2014); https://doi.org/10.1016/j.dyepig.2013.10.022.
C. Liu, T. Miao, L. Zhang, P. Li, Y. Zhang and L. Wang, Asian Chem. J., 25, 2584 (2014); https://doi.org/10.1002/asia.201402274.
T.B. Patrick, T. Juehne, E. Reeb and D. Hennessy, Tetrahedron Lett., 42, 3553 (2001); https://doi.org/10.1016/S0040-4039(01)00526-3.