Generic placeholder image

Letters in Organic Chemistry

Editor-in-Chief

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

Letter Article

On Water Synthesis of 3-Aryl-5,7-dimethyl-1,2,4-triazolo[4,3-a]pyrimidines using Iodobenzene Diacetate

Author(s): Rinku Soni, Deepak Kumar Aneja*, Monika Sihag, Neha Rani and Mayank Kinger

Volume 20, Issue 5, 2023

Published on: 07 December, 2022

Page: [401 - 406] Pages: 6

DOI: 10.2174/1570178620666221025160300

Price: $65

conference banner
Abstract

A simple and green methodology has been developed for the synthesis of 3-aryl-5,7- dimethyl-1,2,4-triazolo[4,3-a]pyrimidines in water. Oxidative cyclization of 4,6-dimethyl-2- pyrimidinylhydrazones of different aldehydes was achieved in good to excellent yield using iodobenzene diacetate at room temperature. High efficiency, easy work-up, short reaction time, non-toxicity of solvent and ambient temperature are the advantages of this methodology.

Graphical Abstract

[1]
Pons, J.; Chadghan, A.; García, A.J. Ros. J. Lett. Org. Chem., 2010, 7(2), 178-181.
[http://dx.doi.org/10.2174/157017810790796273]
[2]
Guerrero, M.; Pons, J.; Font, B.M.; Calvet, T.; Ros, J. J. Chem. Crystallogr., 2011, 41(5), 721-726.
[http://dx.doi.org/10.1007/s10870-010-9960-y]
[3]
Guerrero, M.; Perez, A. Curr. Org. Synth., 2014, 11, 149-155.
[http://dx.doi.org/10.2174/15701794113106660077]
[4]
Kaur, R.; Chaudhary, S.; Kumar, K.; Gupta, M.K.; Rawal, R.K. Eur. J. Med. Chem., 2017, 132, 108-134.
[http://dx.doi.org/10.1016/j.ejmech.2017.03.025] [PMID: 28342939]
[5]
Hammam, A.E.F.G.; Fahmy, A.F.M.; Amr, A.G.E.; Mohamed, A.M. Indian J. Chem., 2003, 42B, 1985-1993.
[6]
Shalaby, A.F.A.; Abdulla, M.M.; Amr, A.E.G.E.; Hussain, A.A. Monatsh. Chem., 2007, 138(10), 1019-1027.
[http://dx.doi.org/10.1007/s00706-007-0701-7]
[7]
Abdel, L.N.A.; Sabry, N.M.; Mohamed, A.M.; Abdulla, M.M. Monatsh. Chem., 2007, 138(7), 715-724.
[http://dx.doi.org/10.1007/s00706-007-0656-8]
[8]
Loev, B.; Musser, J.H.; Brown, R.E.; Jones, H.; Kahen, R.; Huang, F.C.; Khandwala, A.; Sonnino, G.P.; Leibowitz, M.J. J. Med. Chem., 1985, 28(3), 363-366.
[http://dx.doi.org/10.1021/jm00381a016] [PMID: 2579236]
[9]
Gupta, R.; Gupta, A.K.; Paul, S.; Kachroo, P.L. Indian J. Chem., 1998, 37B, 1211-1213.
[10]
Renyu, Q.; Yuchao, L.; Kandegama, W.M.W.W.; Qiong, C.; Guangfu, Y. Mini Rev. Med. Chem., 2018, 18(9), 781-793.
[http://dx.doi.org/10.2174/1389557517666171101112850] [PMID: 29090667]
[11]
Andrea, R.; Chiara, C.; Alessandro, L.; Gioel, G.S.; Alessia, V.; Sara, B.; Roberta, R.; Sandra, B.; Francesco, R.; Angelo, S.B. Recent Adv. Cardiovasc. Drug Discov., 2014, 9, 51-57.
[12]
Maresta, A.; Balducelli, M.; Cantini, L.; Casari, A.; Chioin, R.; Fabbri, M.; Fontanelli, A.; Monici, P.P.A.; Repetto, S.; De Servi, S. Circulation, 1994, 90(6), 2710-2715.
[http://dx.doi.org/10.1161/01.CIR.90.6.2710] [PMID: 7994812]
[13]
Yi, G.; Deval, J.; Fan, B.; Cai, H.; Soulard, C.; Ranjith, K.C.T.; Smith, B. Antimicrob. Agents Chemother., 2012, 56, 830-837.
[http://dx.doi.org/10.1128/AAC.05438-11] [PMID: 22143520]
[14]
Lepiece, D.; Thompson, A.; McReath, A. Wet, 1998, 63, 735-742.
[15]
Yang, G.; Liu, H.; Yang, H. Pestic. Sci., 1999, 55(12), 1143-1150.
[http://dx.doi.org/10.1002/(SICI)1096-9063(199912)55:12<1143:AID-PS28>3.0.CO;2-X]
[16]
Yang, G.; Liu, H.; Yang, X.; Yang, H. Sci. China B Chem., 1999, 42(6), 656-662.
[http://dx.doi.org/10.1007/BF02874332]
[17]
Shaban, M.A.E.; Taha, M.A.M.; Nasr, A.Z.; Morgaan, A.E.A. Pharmazie, 1995, 50, 784-788.
[18]
Turk, C.; Svete, J. Golobič, A.; Golič, L.; Stanovnik, B. J. Heterocycl. Chem., 1998, 35(3), 513-518.
[http://dx.doi.org/10.1002/jhet.5570350304]
[19]
Pollak, A.; Tišler, M. Tetrahedron, 1966, 22(7), 2073-2079.
[http://dx.doi.org/10.1016/S0040-4020(01)82127-X]
[20]
El-Ashry, E.S.H.; Rashed, N. Curr. Org. Chem., 2000, 4, 609-651.
[http://dx.doi.org/10.2174/1385272810004060609]
[21]
Bower, J.D.; Doyle, F.P. J. Chem. Soc., 1957, 141, 727-732.
[http://dx.doi.org/10.1039/jr9570000727]
[22]
Ciesielski, M.; Pufky, D.; Döring, M. Tetrahedron, 2005, 61(24), 5942-5947.
[http://dx.doi.org/10.1016/j.tet.2005.01.111]
[23]
Awad, I.M.A.; Abdel, R.A.E.; Bakhite, E.A. Phosphorus Sulfur Silicon Relat. Elem., 1992, 69(3-4), 213-218.
[http://dx.doi.org/10.1080/10426509208040639]
[24]
Rashed, N.; El Massry, A.M.; El Ashry, E.S.H.; Amer, A.; Zimmer, H. J. Heterocycl. Chem., 1990, 27(3), 691-694.
[http://dx.doi.org/10.1002/jhet.5570270339]
[25]
El-Gazzar, A.B.A. Phosphorus Sulfur Silicon Relat. Elem., 2005, 180(1), 283-293.
[http://dx.doi.org/10.1080/104265090509108]
[26]
Shaban, M.A.; Taha, M.A.; Nasr, A.Z.J. Islamic Acad. Sci, 1990, 3, 98-102.
[27]
Kramberger, L. Lorenčak, P.; Polanc, S.; Verček, B.; Stanovnik, B.; Tišler, M.; Považanec, F. J. Heterocycl. Chem., 1975, 12(2), 337-342.
[http://dx.doi.org/10.1002/jhet.5570120225]
[28]
Butler, R.N.; Johnston, S.M. J. Chem. Soc. Chem. Commun., 1981, (8), 376-377.
[http://dx.doi.org/10.1039/c39810000376]
[29]
Shaban, M.; Nasr, A.; Taha, M. J. Carbohydr. Chem., 1995, 14(7), 985-994.
[http://dx.doi.org/10.1080/07328309508005390]
[30]
Zhdankin, V.V.; Muñiz, K. J. Org. Chem., 2017, 82(22), 11667-11668.
[http://dx.doi.org/10.1021/acs.joc.7b02531] [PMID: 29148275]
[31]
Akiba, K.Y. Chemistry of hypervalent compounds; John Wiley & Sons: United States, 1998.
[32]
Kamal, R.; Kumar, V.; Kumar, R. Chem. Asian J., 2016, 11(14), 1988-2000.
[http://dx.doi.org/10.1002/asia.201600119] [PMID: 27123538]
[33]
Deng, R.; Zhan, S.; Li, C. Gu. Z. Angew. Chem. Int. Ed., 2020, 59(8), 3093-3098.
[http://dx.doi.org/10.1002/anie.201913373]
[34]
Kumar, P. Chem. Heterocycl. Compd., 2012, 47(10), 1237-1243.
[http://dx.doi.org/10.1007/s10593-012-0899-0]
[35]
Prasanna, K.B.N.; Mohana, K.N.; Mallesha, L. Med. Chem. Res., 2014, 23(1), 445-453.
[http://dx.doi.org/10.1007/s00044-013-0656-7]
[36]
Prakash, O.; Bhardwaj, V.; Kumar, R.; Tyagi, P.; Aneja, K.R. Eur. J. Med. Chem., 2004, 39(12), 1073-1077.
[http://dx.doi.org/10.1016/j.ejmech.2004.06.011] [PMID: 15571869]
[37]
Strauss, C.R.; Trainor, R.W. Aust. J. Chem., 1995, 48(10), 1665-1692.
[http://dx.doi.org/10.1071/CH9951665]
[38]
Li, C.J.; Chen, L. Chem. Soc. Rev., 2006, 35(1), 68-82.
[http://dx.doi.org/10.1039/B507207G] [PMID: 16365643]
[39]
Li, C. J. Chem. Rev., 2005, 105(8), 3095-3166.
[http://dx.doi.org/10.1021/cr030009u] [PMID: 16092827]
[40]
Blackmond, D.G.; Armstrong, A.; Coombe, V.; Wells, A. Angew. Chem. Int. Ed., 2007, 46(21), 3798-3800.
[http://dx.doi.org/10.1002/anie.200604952]
[41]
Miyamoto, K.; Yokota, Y.; Suefuji, T.; Yamaguchi, K.; Ozawa, T.; Ochiai, M. Chemistry, 2014, 20(18), 5447-5453.
[http://dx.doi.org/10.1002/chem.201304961] [PMID: 24644216]
[42]
Soni, R.; Sihag, M.; Kinger, M.; Aneja, D.K. Indian J. Heterocycl. Chem., 2021, 31, 141-153.
[43]
Soni, R.; Sihag, M.; Rani, N.; Kinger, M.; Aneja, D.K. Asian J. Org. Chem., 2022, 11, e202200125.
[44]
Erkin, A.V.; Krutikov, V.I. Russ. J. Gen. Chem., 2009, 79(4), 872-873.
[http://dx.doi.org/10.1134/S1070363209040355]
[45]
Gupta, S.; Pal, S.; Barik, A.K.; Hazra, A.; Roy, S.; Mandal, T.N.; Peng, S.M.; Lee, G.H.; Salah El Fallah, M.; Tercero, J.; Kar, S.K. Polyhedron, 2008, 27(12), 2519-2528.
[http://dx.doi.org/10.1016/j.poly.2008.05.009]
[46]
Kosolapoff, G.M.; Roy, C.H. J. Org. Chem., 1961, 26(6), 1895-1898.
[http://dx.doi.org/10.1021/jo01065a049]
[47]
Nelson, D.J.; Washington, D.C. U.S. Patent 7,220,858, 2007.
[48]
Ostrovskii, V.A.; Danagulyan, G.G.; Nesterova, O.M.; Pavlyukova, Y.N.; Tolstyakov, V.V.; Zarubina, O.S.; Slepukhin, P.A.; Esaulkova, Y.L.; Muryleva, A.A.; Zarubaev, V.V.; Trifonov, R.E. Chem. Heterocycl. Compd., 2021, 57(4), 448-454.
[http://dx.doi.org/10.1007/s10593-021-02922-6]

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy