Login Register Cart 0
Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Back
Journal Home About Journal Editorial Board Journal Insight Current Issue Volumes/Issues
Subscribe
Research Article

Simple, Stepwise and Alternative Syntheses of Indolyl Triazoles via Huisgen,s 1, 3-dipolar Cycloaddition Reaction

Author(s): Ch. Venkata Ramana Reddy* and G. Ganga Reddy

Volume 18, Issue 3, 2021

Published on: 25 February, 2020

Page: [187 - 194] Pages: 8

DOI: 10.2174/1570178617666200225110402

Price: $65

Abstract

A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol- 3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3-dipolar cycloaddition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures, and shorter reaction time. These reactions are very facile, giving products by simple processing that does not require purification by column chromatography. Spectroscopic methods confirmed all the newly synthesized compounds.

Keywords: Knoevengal condensation, 1, 2, 3-triazole, N-propargylation, click chemistry, Aryl azides, step-wise synthesis and alternative synthesis.

« Previous Next »
Graphical Abstract

[1]
Sha, C.K.; Mohanakrishnan, A. K. Wiley New York, 2003, 623-679.
[2]
Kamal, A.; Shankaraiah, N.; Devaiah, V.; Laxma Reddy, K.; Juvekar, A.; Sen, S.; Kurian, N.; Zingde, S. Bioorg. Med. Chem. Lett., 2008, 18(4), 1468-1473.
[http://dx.doi.org/10.1016/j.bmcl.2007.12.063] [PMID: 18207392]
[3]
Alvarez, R.; Velázquez, S.; San-Félix, A.; Aquaro, S.; De Clercq, E.; Perno, C-F.; Karlsson, A.; Balzarini, J.; Camarasa, M.J. J. Med. Chem., 1994, 37(24), 4185-4194.
[http://dx.doi.org/10.1021/jm00050a015] [PMID: 7527463]
[4]
da Silva, F. de C.; de Souza, M.C.B.V.; Frugulhetti, I.I.P.; Castro, H.C.; Souza, S.L. de O.; de Souza, T.M.; Rodrigues, D.Q.; Souza, A.M.; Abreu, P.A.; Passamani, F.; Rodrigues, C.R.; Ferreira, V.F. Eur. J. Med. Chem., 2009, 44(1), 373-383.
[http://dx.doi.org/10.1016/j.ejmech.2008.02.047] [PMID: 18486994]
[5]
Thomas, K.D.; Adhikari, A.V.; Shetty, N.S. Eur. J. Med. Chem., 2010, 45(9), 3803-3810.
[http://dx.doi.org/10.1016/j.ejmech.2010.05.030] [PMID: 20542604]
[6]
Hoshino, M. Nature, 1960, 186, 174-175.
[http://dx.doi.org/10.1038/186174a0] [PMID: 14403295]
[7]
Wang, G.; Peng, Z.; Wang, J.; Li, J.; Li, X. Bioorg. Med. Chem. Lett., 2016, 26(23), 5719-5723.
[http://dx.doi.org/10.1016/j.bmcl.2016.10.057] [PMID: 27810241]
[8]
Jordão, A.K.; Ferreira, V.F.; Lima, E.S.; de Souza, M.C.B.V.; Carlos, E.C.L.; Castro, H.C.; Geraldo, R.B.; Rodrigues, C.R.; Almeida, M.C.; Cunha, A.C. Bioorg. Med. Chem., 2009, 17(10), 3713-3719.
[http://dx.doi.org/10.1016/j.bmc.2009.03.053] [PMID: 19380229]
[9]
Hou, D-R.; Alam, S.; Kuan, T-C.; Ramanathan, M.; Lin, T-P.; Hung, M-S. Bioorg. Med. Chem. Lett., 2009, 19(3), 1022-1025.
[http://dx.doi.org/10.1016/j.bmcl.2008.11.029] [PMID: 19095444]
[10]
Shen, J.; Woodward, R.; Kedenburg, J.P.; Liu, X.; Chen, M.; Fang, L.; Sun, D.; Wang, P.G. J. Med. Chem., 2008, 51(23), 7417-7427.
[http://dx.doi.org/10.1021/jm8005355] [PMID: 19007204]
[11]
Périon, R.; Ferrières, V.; García-Moreno, M.I.; Ortiz Mellet, C.; Duval, R.; García Fernández, J.M.; Plusquellec, D. Tetrahedron, 2005, 61, 9118.
[http://dx.doi.org/10.1016/j.tet.2005.07.033]
[12]
Genin, M.J.; Allwine, D.A.; Anderson, D.J.; Barbachyn, M.R.; Emmert, D.E.; Garmon, S.A.; Graber, D.R.; Grega, K.C.; Hester, J.B.; Hutchinson, D.K.; Morris, J.; Reischer, R.J.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H. J. Med. Chem., 2000, 43(5), 953-970.
[http://dx.doi.org/10.1021/jm990373e] [PMID: 10715160]
[13]
Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem. Int. Ed. Engl., 2001, 40(11), 2004-2021.
[http://dx.doi.org/10.1002/1521-3773(20010601)40:11<2004:AID-ANIE2004>3.0.CO;2-5] [PMID: 11433435]
[14]
(a)Rostovtsev, V.V.; Green, L.G.; Fokin, V.V.; Sharpless, K.B. Angew. Chem. Int. Ed. Engl.,, 2002, 41(14), 2596-2599.
[http://dx.doi.org/10.1002/1521-3773(20020715)41:142596::AIDANIE2596>3.0.CO;2-4] [PMID: 12203546]
(b)Kolb, H.C.; Sharpless, K.B. Drug Discov. Today, 2003, 8(24),1128-1137,,
[http://dx.doi.org/10.1016/S1359-6446(03)02933-7] [PMID: 14678739]
(c)Rodionov, V.O.; Presolski, S.I.; Díaz, D.D.; Fokin, V.V.; Finn, M.G. J. Am. Chem. Soc., 2007, 129(42), 12705-12712.
[http://dx.doi.org/10.1021/ja072679d] [PMID: 17914817]
[15]
Chassaing, S.; Kumarraja, M.; Souna Sido, A.S.; Pale, P. Sommer. J. Org. Lett., 2007, 9(5), 883-886.
[http://dx.doi.org/10.1021/ol0631152] [PMID: 17286410]
[16]
Lipshutz, B.H.; Taft, B.R. Angew. Chem. Int. Ed. Engl., 2006, 45(48), 8235-8238.
[http://dx.doi.org/10.1002/anie.200603726] [PMID: 17111447]
[17]
Candeon, N.; Lastecoueres, D.; Diallo, A.K.; Aranzaes, J.R.; Astruc, D.; Vincent, J.M. Chem. Commun., 2008, 741.
[18]
Wender, P.A.; Handy, S.T.; Wright, D.L. Chem. Ind., 1997, 19, 765.
[19]
Kolb, H.C.; Finn, M.G.; Sharpless, K.B. Angew. Chem., 2001, 113, 2056.
[20]
Tornøe, C.W.; Christensen, C.; Meldal, M. J. Org. Chem., 2002, 67(9), 3057-3064.
[http://dx.doi.org/10.1021/jo011148j] [PMID: 11975567]
[21]
Kumar, D.; Patel, G.; Reddy, B.V. Synlett, 2009, 18, 399.
[http://dx.doi.org/10.1055/s-0028-1087556]
[22]
Firouzeh, N.; Ali, E.J. Appl Che., 2012, 7, 23.
[23]
Yu, J.Z.; Yanchang, Y.S. Synth. Commun., 1990, 20, 3277-3282.
[http://dx.doi.org/10.1080/00397919008051559]
[24]
Fraser, F.; Lihua, P.C.; Ravikumar, L.F.; Brian, C.S. J. Med. Chem., 2010, 7902-7917.
[25]
Venkatanarayana, M.; Dubey, P.K. Synth. Commun., 2012, 42, 1746-1759.
[http://dx.doi.org/10.1080/00397911.2010.543382]

Rights & Permissions Print Cite
Article Metrics
11
1
© 2024 Bentham Science Publishers | Privacy Policy