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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

A Novel One-pot Protocol for the Cu-Catalyzed Synthesis of Nine 2-Aminobenzimidazole Derivatives from o-Phenylenediamine and Trichloroacetonitrile

Author(s): Manijeh Nematpour*, Elham Abedi and Elahe Abedi

Volume 16, Issue 2, 2019

Page: [99 - 103] Pages: 5

DOI: 10.2174/1570178615666180914114010

Price: $65

Abstract

The synthesis of a variety of 2-aminobenzimidazoles via a one pot reaction of ophenylenediamine and trichloroacetonitrile catalyzed by copper (II) acetate in THF at room temperature, with good yields is described. Use of simple and readily available starting materials, good to high yields, free ligand, and no column chromatography are important features of this protocol.

Keywords: Trichloroacetonitrile, copper (II) acetate, 2-aminobenzimidazoles, o-phenylenediamine, THF, ligand.

Graphical Abstract
[1]
(a) Kling, A.; Backfisch, G.; Delzer, J.; Geneste, H.; Graef, C.; Hornberger, W.; Lange, U.; Lauterbach, A.; Seitz, W.; Subkowski, T. Bioorg. Med. Chem., 2003, 11, 1319.
(b) Beaulieu, C.; Wang, Z.; Denis, D.; Greig, G.; Lamontagne, S.; O’Neill, G.; Slipetz, D.; Wang, J. Bioorg. Med. Chem. Lett., 2004, 14, 3195.
(c) Snow, R.J.; Cardozo, M.G.; Morwick, T.M.; Busacca, C.A.; Dong, Y.; Eckner, R.J.; Jacober, S.; Jakes, S.; Kapadia, S.; Lukas, S.; Panzenbeck, M.; Peet, G.W.; Peterson, J.D.; Prokopowicz, A.S.; Sellati, R.; Tolbert, R.M.; Tschantz, M.A.; Moss, N. J. Med. Chem., 2002, 45, 3394.
[2]
Madden, J.; Dod, J.R.; Godemann, R.; Kraemer, J.; Smith, M.; Biniszkiewicz, M.; Hallett, D.J.; Barker, J.; Dyekjaer, D.J.; Hesterkamp, T. Bioorg. Med. Chem. Lett., 2010, 20, 5329.
[3]
Punit, P.S.; Elizabeth, A.J.; Lisa, M.R.; Stephen, A.O. Bioorg. Med. Chem. Lett., 2003, 13, 1669.
[4]
Zhong, M.; Bui, M.; Shen, W.; Baskaran, S.; Allen, D.A.; Elling, R.A.; Flanagan, M.; Fung, A.D.; Hanan, E.J.; Harris, S.O.; Heumann, S.A.; Hoch, U.; Sheryl, N.I.; Jacobs, J.W.; Stuart, L.; Lee, M.; McDowell, R.S.; Oslob, J.D.; Purkey, H.E.; Romanowski, M.J.; Silverman, J.A.; Tangonan, B.T.; Pietro, T.; Yang, W.; Yoburn, J.C.; Yu, C.H.; Zimmerman, K.M.; O’Brien, T.; Lew, W. Bioorg. Med. Chem. Lett., 2009, 19, 5158.
[5]
(a) Bachmann, K.A. Curr. Opin. Investig. Drugs, 2000, 1, 219.
(b) Armstrong, S.C.; Cozza, K.L. Psychosomatics, 2003, 44, 430.
[6]
(a) Valdez, J.; Cedillo, R.; Hernández-Campos, A.; Yépez, L.; Hernández-Luis, F.; Navarrete-Vázquez, G.; Tapia, A.; Cortés, R.; Hernández, M.; Castillo, R. Bioorg. Med. Chem. Lett., 2002, 12, 2221.
(b) Powers, J.P.; Li, S.; Jaen, J.C.; Liu, J.; Walker, N.P.C.; Wang, Z.; Wesche, H. Bioorg. Med. Chem. Lett., 2006, 16, 2842.
(c) Ella, D.A.E.; Goßnitzer, E.; Wendelin, W. J. Heterocycl. Chem., 1996, 33, 373.
[7]
(a) Wang, F.; Cai, S.; Liao, Q.; Xi, C. J. Org. Chem., 2011, 76, 3174.
(b) Saha, P.; Ramana, T.; Purkait, N.; Ali, M.A.; Paul, R.; Punniyamurthy, P. J. Org. Chem., 2009, 74, 8719.
(c) Shen, G.; Bao, W. Adv. Synth. Catal., 2010, 352, 981.
[8]
(a) Wan, Z.K.; Ousman, E.F.; Papaioannou, N.; Saiah, E. Tetrahedron Lett., 2011, 52, 4149.
(b) Narsaiah, A.V.; Reddy, A.R.; Yadav, J.S. Synth. Commun., 2010, 40, 1750.
(c) Scheffer, U.; Strick, A.; Ludwig, V.; Peter, S.; Kalden, E.; Gobel, M.W. J. Am. Chem. Soc., 2005, 127, 2211.
[9]
Zhu, T.H.; Wang, S.Y.; Wang, G.N.; Ji, S.J. Chem. Eur. J., 2013, 19, 5850.
[10]
Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett.,2009, 11, 1607; (b) Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc.,2010, 132, 6900; (c) Matsuda, N.; Hirano, K.; Satoh, T.; Miura, M. Org. Lett.,2011, 13, 2860; (d) Wang, Q.; Schreiber, S.L. Org. Lett., 2009, 11, 5178.
[11]
(a) Yavari, I.; Nematpour, M.; Damghani, T. Mol. Divers., 2013, 17, 801.
(b) Yavari, I.; Nematpour, M. Mol. Divers., 2012, 16, 651.
(c) Yavari, I.; Nematpour, M. Synlett, 2013, 24, 165.
(d) Nematpour, M.; Abedi, E.; Abedi, E. Phosphorus Sulfur Silicon., 2017, 192, 387.
(e) Nematpour, M.; Abedi, E.; Lotfi, M. Phosphorus Sulfur Silicon, 2017, 192, 427.
(f) Nematpour, M.; Abedi, E.; Abedi, E. Lett. Org. Chem., 2018, 15, 678.
[12]
Frei, R.; Breitbach, A.S.; Blackwell, H.E. Angew. Chem. Int. Ed., 2012, 51, 5226.

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