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Letters in Organic Chemistry

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

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Letter Article

On Water Synthesis of 3-Aryl-1,2,4-Triazolo[4,3-a]Pyridines Using Iodobenzene Diacetate (IBD)

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

Volume 20, Issue 7, 2023

Published on: 08 February, 2023

Page: [608 - 611] Pages: 4

DOI: 10.2174/1570178620666230110111547

Price: $65

Abstract

An iodobenzene diacetate (IBD)-mediated simple and green method was determined for the intramolecular oxidative cyclization of 3-aryl-2-pyridiylhydrazones of different aromatic aldehydes in an aqueous medium at room temperature. This efficient strategy provides a route to the synthesis of 3-aryl-1,2,4-triazolo[4,3-a]pyridines in water which eliminates the requirement to use costly and unsafe volatile organic solvents. All reactions were carried out by just stirring the reaction components in water at room temperature. This protocol provides a wide substrate scope and good functional group tolerance.

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[1]
Bhadoriya, U.; Jain, D.K. Indian J. Heterocycl. Chem., 2018, 28, 407-417.
[2]
Bhatt, A.; Singh, R.K.; Kant, R. Chem. Biol. Lett., 2017, 4, 73-80.
[3]
Bhat, K.S.; Poojary, B.; Prasad, D.J.; Naik, P.; Holla, B.S. Eur. J. Med. Chem., 2009, 44(12), 5066-5070.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.010] [PMID: 19822384]
[4]
Naito, Y.; Akahoshi, F.; Takeda, S.; Okada, T.; Kajii, M.; Nishimura, H.; Sugiura, M.; Fukaya, C.; Kagitani, Y. J. Med. Chem., 1996, 39(15), 3019-3029.
[http://dx.doi.org/10.1021/jm9507993] [PMID: 8709136]
[5]
Papakonstantinou-Garoufalias, S.; Pouli, N.; Marakos, P.; Chytyroglou-Ladas, A. Farmaco, 2002, 57(12), 973-977.
[http://dx.doi.org/10.1016/S0014-827X(02)01227-2] [PMID: 12564470]
[6]
Navidpour, L.; Shadnia, H.; Shafaroodi, H.; Amini, M.; Dehpour, A.R.; Shafiee, A. Bioorg. Med. Chem., 2007, 15(5), 1976-1982.
[http://dx.doi.org/10.1016/j.bmc.2006.12.041] [PMID: 17258905]
[7]
Saha, A.K.; Liu, L.; Simoneaux, R.; DeCorte, B.; Meyer, C.; Skrzat, S.; Breslin, H.J.; Kukla, M.J.; End, D.W. Bioorg. Med. Chem. Lett., 2005, 15(24), 5407-5411.
[http://dx.doi.org/10.1016/j.bmcl.2005.09.007] [PMID: 16216509]
[8]
De Clercq, E. J. Clin. Virol., 2004, 30(2), 115-133.
[http://dx.doi.org/10.1016/j.jcv.2004.02.009] [PMID: 15125867]
[9]
Collin, X.; Sauleau, A.; Coulon, J. Bioorg. Med. Chem. Lett., 2003, 13(15), 2601-2605.
[http://dx.doi.org/10.1016/S0960-894X(03)00378-0] [PMID: 12852975]
[10]
Hester, J.B., Jr; Rudzik, A.D.; Kamdar, B.V. J. Med. Chem., 1971, 14(11), 1078-1081.
[http://dx.doi.org/10.1021/jm00293a015] [PMID: 5165540]
[11]
Dash, C.; Shaikh, M.M.; Ghosh, P. J. Chem. Sci., 2011, 123(2), 97-106.
[http://dx.doi.org/10.1007/s12039-011-0105-4]
[12]
Kumar, P. Chem. Heterocycl. Compd., 2012, 47(10), 1237-1243.
[http://dx.doi.org/10.1007/s10593-012-0899-0]
[13]
Prasanna Kumara, 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]
[14]
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]
[15]
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]
[16]
Manabe, K.; Iimura, S.; Sun, X.M.; Kobayashi, S. J. Am. Chem. Soc., 2002, 124(40), 11971-11978.
[http://dx.doi.org/10.1021/ja026241j] [PMID: 12358542]
[17]
Tsukinoki, T.; Nagashima, S.; Mitoma, Y.; Tashiro, M. Green Chem., 2000, 2(3), 117-119.
[http://dx.doi.org/10.1039/b001533o]
[18]
Soni, R.; Sihag, M.; Kinger, M.; Aneja, D.K. Indian J. Heterocycl. Chem., 2021, 31, 141-153.
[19]
Soni, R.; Sihag, M.; Rani, N.; Kinger, M.; Aneja, D.K. Asian J. Org. Chem., 2022, 11e202200125
[20]
Todeschini, A.R.; de Miranda, A.L.P.; da Silva, K.C.M.; Parrini, S.C.; Barreiro, E.J. Eur. J. Med. Chem., 1998, 33(3), 189-199.
[http://dx.doi.org/10.1016/S0223-5234(98)80008-1]
[21]
Bower, J.D.; Doyle, F.P. J. Chem. Soc., 1957, 141, 727-732.
[http://dx.doi.org/10.1039/jr9570000727]
[22]
Sadana, A.K.; Mirza, Y.; Aneja, K.R.; Prakash, O. Eur. J. Med. Chem., 2003, 38(5), 533-536.
[http://dx.doi.org/10.1016/S0223-5234(03)00061-8] [PMID: 12767604]
[23]
Naqui, S.; Srinivasan, V.R. J. Sci. Ind. Res., 1962, 21, 456.
[24]
Naqui, S.S.; Srinivas, V.R. Indian J. Chem., 1965, 3, 162.
[25]
Ciesielski, M.; Pufky, D.; Döring, M. Tetrahedron, 2005, 61(24), 5942-5947.
[http://dx.doi.org/10.1016/j.tet.2005.01.111]
[26]
Padalkar, V.S.; Patil, V.S.; Phatangare, K.R.; Umape, P.G.; Sekar, N. Synth. Commun., 2011, 41(6), 925-938.
[http://dx.doi.org/10.1080/00397911003707162]
[27]
Al-Qallaf, M.A.; Dib, H.H.; Al-Awadi, N.A.; El-Dusouqui, O.M.E. J. Anal. Appl. Pyrolysis, 2017, 124, 446-453.
[http://dx.doi.org/10.1016/j.jaap.2017.02.021]
[28]
Bhatt, A.; Singh, R.K.; Kant, R. Chem. Heterocycl. Compd., 2018, 54(12), 1111-1116.
[http://dx.doi.org/10.1007/s10593-019-02400-0]
[29]
Crljenak, S.I.; Tabakovic, D. Acta Chem. Scand. , 1983, 37(6), 459-466.

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