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

A Facile and Efficient Synthesis of bis(Imidazo[1,2-a]pyridin-3-yl)methane and Vinyl Derivatives

Author(s): Daliparthi Eswara Prasada Rao, Medepalli David Raju, Jasti Surendra, Ala Vasu Babu, Poguri Eswaraiah, Nallamaddi Ravi Kumar Reddy, Chinnapillai Rajendiran and Mandava Venkata Basaveswara Rao*

Volume 19, Issue 1, 2022

Page: [53 - 58] Pages: 6

DOI: 10.2174/1570178618666211022144225

Price: $65

Abstract

An efficient synthetic route for the novel bis-imdizo[1,2-a]pyridine-3-yl)methane (2a-k) derivatives have been developed using acetic acid and two drops of trifluoroacetic acid at 40-45oC, resulting in 60-72% yields. An attempt to synthesize bis(Imidazo[1,2-a]pyridin-3-yl)methyl chloride derivatives by the reaction between two moles of imidazo[1,2-a]pyridine, one mole of chloroacetaldehyde in acetic acid, and two drops of trifluoroacetic acid was not successful, instead underwent dehydrohalogenation to yield vinyl derivatives (4a-d).

Keywords: Bis-imidazo[1, 2-a]pyridine, bis(Imidazo[1, 2-a]pyridin-3-yl) methane, 2-a]pyridin-3-yl)vinyl derivatives, Synthesis, antiviral agent, anti-inflammatory agent.

« Previous Next »
Graphical Abstract

[1]
Anderson, M.; Beattie, J.F.; Breault, G.A.; Breed, J.; Byth, K.F.; Culshaw, J.D.; Ellston, R.P.; Green, S.; Minshull, C.A.; Norman, R.A.; Pauptit, R.A.; Stanway, J.; Thomas, A.P.; Jewsbury, P.J. Bioorg. Med. Chem. Lett., 2003, 13(18), 3021-3026.
[http://dx.doi.org/10.1016/S0960-894X(03)00638-3] [PMID: 12941325]
[2]
Hempel, G.; Blaschke, G. J. Chromatogr. B Biomed. Appl., 1996, 675(1), 131-137.
[http://dx.doi.org/10.1016/0378-4347(95)00342-8] [PMID: 8634754]
[3]
Trapani, G.; Latrofa, A.; Franco, M.; Carrieri, A.; Cellamare, S.; Serra, M.; Sanna, E.; Biggio, G.; Liso, G. Eur. J. Pharm. Sci., 2003, 18(3-4), 231-240.
[http://dx.doi.org/10.1016/S0928-0987(03)00002-2] [PMID: 12659934]
[4]
Lacerda, R.B.; de Lima, C.K.; da Silva, L.L.; Romeiro, N.C.; Miranda, A.L.; Barreiro, E.J.; Fraga, C.A. Bioorg. Med. Chem., 2009, 17(1), 74-84.
[http://dx.doi.org/10.1016/j.bmc.2008.11.018] [PMID: 19059783]
[5]
Gueiffier, A.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.C.; Kerbal, A.; Essassi, E.M.; Debouzy, J.C.; Witvrouw, M.; Blache, Y.; Balzarini, J.; De Clercq, E.; Chapat, J.P. J. Med. Chem., 1996, 39(14), 2856-2859.
[http://dx.doi.org/10.1021/jm9507901] [PMID: 8709116]
[6]
Gueiffier, A.; Mavel, S.; Lhassani, M.; Elhakmaoui, A.; Snoeck, R.; Andrei, G.; Chavignon, O.; Teulade, J.C.; Witvrouw, M.; Balzarini, J.; De Clercq, E.; Chapat, J.P. J. Med. Chem., 1998, 41(25), 5108-5112.
[http://dx.doi.org/10.1021/jm981051y] [PMID: 9836626]
[7]
Mavel, S.; Renou, J.L.; Galtier, C.; Allouchi, H.; Snoeck, R.; Andrei, G.; De Clercq, E.; Balzarini, J.; Gueiffier, A. Bioorg. Med. Chem., 2002, 10(4), 941-946.
[http://dx.doi.org/10.1016/S0968-0896(01)00347-9] [PMID: 11836102]
[8]
Sanghani, S.G.; Ganatra, K.J. Pharma Chem., 2010, 2, 378-388.
[9]
Price, S.; Heald, R.; Lee, W.; Zak, M. E.; Hewitt, J. F. M. PCT Int. Appl., WO 2009085983, 2009.
[10]
Hosni, H.M.; Abdulla, M.M. Acta Pharm., 2008, 58(2), 175-186.
[http://dx.doi.org/10.2478/v10007-008-0005-4] [PMID: 18515227]
[11]
Cesur, Z.; Cesur, N.; Birteksöz, S.; Otük, G. Acta Chim. Slov., 2010, 57(2), 355-362.
[PMID: 24061731]
[12]
Rida, S.M.; El-Hawash, S.A.M.; Fahmy, H.T.Y.; Hazzaa, A.A.; El-Meligy, M.M. Arch. Pharm. Res., 2006, 29(10), 826-833.
[http://dx.doi.org/10.1007/BF02973901] [PMID: 17121175]
[13]
Ismail, M.A.; Arafa, R.K.; Wenzler, T.; Brun, R.; Tanious, F.A.; Wilson, W.D.; Boykin, D.W. Bioorg. Med. Chem., 2008, 16(2), 683-691.
[http://dx.doi.org/10.1016/j.bmc.2007.10.042] [PMID: 17976993]
[14]
Ash, A.B.; Stevens, C.L.; Markovac, A. US3600396, 1971.
[15]
Heerding, D.A.; Clark, T.J.; Drewry, D.H.; Leber, J.D.; Safonov, I.; Yamashita, D.S. WO 2005011700, 2005.
[16]
Ohtsuka, M.; Haginoya, N.; Chikawa, M.; Matsunaga, H.; Saito, H.; Shibata, Y.; Tsunemi, T. WO 2010016490, 2010.
[17]
Zhang, R.; Hu, Y. Synth. Commun., 2004, 34, 3955-3962.
[http://dx.doi.org/10.1081/SCC-200034812]
[18]
Sumalatha, Y.; Reddy, P.P.; Reddy, R.; Satyanarayana, B. ARKIVOC, 2009, 8, 143-149.
[http://dx.doi.org/10.3998/ark.5550190.0010.714]
[19]
da Silva, F.M.; Menezes, F.G.; Vicente, J.; Adailton, J.B.; Cesar, Z.; Ademir, N.; Sanches, N.G. J. Mol. Struct., 2009, 938, 1-9.
[http://dx.doi.org/10.1016/j.molstruc.2009.08.031]
[20]
Oi, W.; Nishiki, M.; Ito, K. Lett. Org. Chem., 2007, 2, 112-119.
[http://dx.doi.org/10.2174/157017807780414136]
[21]
Surya, G.K.P.; Fogassy, G.; Olah, G.A. Catal. Lett., 2010, 138, 155-159.
[http://dx.doi.org/10.1007/s10562-010-0406-0]
[22]
Sun, C.; Zou, X.; Li, F. Chemistry, 2013, 19(42), 14030-14033.
[http://dx.doi.org/10.1002/chem.201301555] [PMID: 24108592]
[23]
Durantini, E.N. Molecules, 2001, 6, 533-539.
[http://dx.doi.org/10.3390/60600533]
[24]
Chang-Hee, L.; Lindsey, J.S. Tetrahedron, 1994, 50, 11427-11440.
[http://dx.doi.org/10.1016/S0040-4020(01)89282-6]

Rights & Permissions Print Cite
Article Metrics
18
1
© 2024 Bentham Science Publishers | Privacy Policy