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Letters in Organic Chemistry

Editor-in-Chief

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

Research Article

Zinc Sulfamate Catalyzed Efficient Selective Synthesis of Benzimidazole Derivatives under Ambient Conditions

Author(s): Sushil R. Mathapati, Arvind H. Jadhav*, Mantosh B. Swami and Jairaj K. Dawle*

Volume 16, Issue 9, 2019

Page: [740 - 749] Pages: 10

DOI: 10.2174/1570178616666181211094040

Price: $65

Abstract

Zinc sulfamate (Zn(NH2SO3)2 is a derivative of sulfamic acid (H3NSO3) which possesses “Lewis acidity” and finds well suited in a number of catalytic applications. The present paper describes an efficient, eco-friendly, and clean synthesis of 2-substituted benzimidazole derivatives by reacting diverse o-phenylenediamine with various substituted aromatic aldehydes using a catalytic amount of zinc sulfamate in ethanol at ambient temperature. As a result, 10 mol.% of Zinc sulfamate catalyst showed 92% of respective product yield with 100% conversion using short reaction period in ethanol. Meanwhile, effect of reaction parameters, such as amount of catalyst, different solvents, and reaction temperature on reaction product, was also studied. In addition, in the optimized reaction condition various substituted biological important benzimidazoles derivatives were prepared by using optimized reaction condition in good to efficient yield. In addition, possible reaction mechanism in the presence of zinc sulfamate for the preparation of benzimidazole derivative was sketched and discussed. The present green approach showed significances with faster reaction rate with inexpensive catalyst, which showed excellent and clean yield of benzimidazole in mild reaction condition with easy work-up procedure.

Keywords: Benzimidazole derivatives, zincsulfamate, diamine reaction, green efficient catalysis, ambient reaction conditions, selective derivative preparation.

Graphical Abstract
[1]
Wang, M.; Han, X.; Zhou, Z. Expert Opin. Ther. Pat., 2015, 25, 595-612.
[2]
María, L.; López, R.; Bellinda, B.; Morcillo, M.J.; Tejada, I.D.; Orensanz, L.; Alfaro, M.J.; Martín, M.I.J. Med. Chem., 1999, 42, 5020-5028.
[3]
Sondhi, S.M.; Singh, N.; Kumar, A.; Lozachc, O.; Meijer, L. Bioorg. Med. Chem., 2006, 14, 3758-3765.
[4]
Kus, C.; Kilcigil, G.A.; Ozbey, S.; Kaynak, F.B.; Kaya, M.; Coban, T.; Can-Eke, B. Bioorg. Med. Chem., 2008, 16, 4294-4303.
[5]
Vinodkumar, R.; Vaidya, S.D.; Kumar, B.V.; Bhise, U.N.; Bhirud, S.B.; Mashelkar, U.C. Eur. J. Med. Chem., 2008, 43, 986-995.
[6]
Zarrinmayeh, H.; Zimmerman, D.M.; Cantrell, B.E.; Smith, E.C.R.; Nixon, J.A.; Bruns, R.F.; Gitter, B.; Hipskind, P.A.; Ornestein, P.L.; Zarrinmayeh, H.; Britton, T.C.; Schober, D.A.; Gehlert, D.R. Bioorg. Med. Chem. Lett., 1999, 9, 647-652.
[7]
Camacho, J.; Barazarte, A.; Gamboa, N.; Rodrigues, J.; Rojas, R.; Vaisberg, A.; Gilman, R. Bioorg. Med. Chem., 2011, 19, 2023-2029.
[8]
Berrada, M.; Carriere, F.; Abboud, Y.; Abourriche, A.; Benamara, A.; Lajrhed, N.; Kabbaj, M.; Berrada, M. J. Mater. Chem., 2002, 12, 3551-3559.
[9]
Barker, H.A.; Smyth, R.D.; Weissbach, H.; Toohey, J.I.; Ladd, J.N.; Volcani, B.E. J. Biol. Chem., 1960, 235, 480-488.
[10]
Kidwai, M.; Jahan, A.; Bhatnagar, D. J. Chem. Sci., 2012, 122, 607-612.
[11]
Smith, J.G.; Ho, I. Tetrahedron Lett., 1971, 12, 3541-3544.
[12]
Qu, Y.; Pan, L.; Wu, Z.; Zhou, X. Tetrahedron, 2013, 69, 1717-1719.
[13]
Brain, C.T.; Brunton, S.A. Tetrahedron Lett., 2002, 43, 1893-1895.
[14]
Yang, D.; Fokas, D.; Li, J.; Yu, L.; Baldino, C.M. Synthesis, 2005, 1, 47-56.
[15]
Su, Y.S.; Sun, C.M. Synlett, 2005, 8, 1243-1246.
[16]
Su, Y.S.; Lin, M.J.; Sun, M.C. Tetrahedron Lett., 2005, 46, 177-180.
[17]
Olguin, L.F.; Jimenez-Estrada, M.; Barzana, E.; Navarro-Ocana, A. Synlett, 2005, 2, 340-342.
[18]
Nagata, K.; Itoh, T.; Ishikawa, H.; Ohsawax, A. Heterocycles, 2003, 61, 93-96.
[19]
Bahrami, K.; Khodaei, M.M.; Kavianinia, I. Synthesis, 2007, 4, 417-424.
[20]
Zhang, Z.H.; Li, T.S.; Li, J.J. Monatsh. Chem., 2007, 138, 89-94.
[21]
Chakrabarty, M.; Karmakar, S.; Ajanta, M.; Arima, S.; Harigaya, Y. Heterocycles, 2006, 68, 967-974.
[22]
Salehi, P.; Dabiri, M.; Zolfigol, M.A.; Otokesh, S.; Baghbanzadeh, M. Tetrahedron Lett., 2006, 47, 2557-2560.
[23]
Swami, M.B.; Patil, S.G.; Mathapati, S.R.; Ghuge, H.G.; Jadhav, A.H. Der Pharma Chemica., 2015, 7, 533-535.
[24]
Jadhav, A.H.; Kim, H. RSC Adv., 2013, 15, 5131-5140.
[25]
Nadaf, R.N.; Siddiqui, S.A.; Daniel, T.; Lahoti, R.J.; Srinivasan, K.V. J. Mol. Catal. A: Chem., 2004, 214, 155-160.
[26]
Alibeik, M.A.; Moosavifard, M. Synth. Commun., 2010, 40, 2686-2695.
[27]
Jadhav, A.H.; Chinnappan, A.; Hiremath, V.; Seo, J.G. J. Nanosci. Nanotechnol., 2015, 15, 8243-8250.
[28]
Jacob, R.G.; Dutra, L.G.; Radatz, C.S.; Mendes, S.R.; Perin, G.; Lenardao, E.J. Tetrahedron Lett., 2009, 50, 1495-1497.
[29]
Khan, A.T.; Parvin, T.; Choudhury, L.H. Synth. Commun., 2009, 39, 2339-2346.
[30]
Narsaiah, V.; Reddy, A.R.; Yadav, J.S. Synth. Commun., 2011, 4, 262-267.
[31]
Trivedi, R.; De, S.K.; Gibbs, R.A. J. Mol. Catal. A: Chem., 2006, 245, 8-11.
[32]
Vazquez, G.N.; Diaz, H.M.; Soto, S.E. Synth. Commun., 2007, 37, 2815-2825.
[33]
Hasaninejad, A.; Niknam, K.; Zare, A.; Farsimadan, E.; Shekouhy, M. Phosphorus Sulfur Silicon Relat. Elem., 2009, 184, 147-155.
[34]
Kumar, A.; Maurya, R.A.; Saxena, D. Mol. Divers., 2010, 14, 331-341.
[35]
Padalkar, V.S.; Gupta, V.D.; Phatangare, K.R.; Patil, K.R.; Umape, V.S.; Sekar, P.G. Green Chem. Lett. Rev., 2012, 5, 139-145.
[36]
Sharghi, H.; Asemani, O.; Khalifeh, R. Synth. Commun., 2008, 38, 1128-1136.
[37]
Lei, M.; Ma, L.; Hu, L. Synth. Commun., 2012, 42, 2981-2993.
[38]
Bahrami, K.; Khodaei, M.M.; Nejati, A. Green Chem., 2010, 12, 1237-1241.
[39]
Jadhav, A.H.; Mai, X.T.; Ntiamoah, A.P.; Lee, H.; Momade, F.W.Y.; Seo, J.G.; Kim, H. J. Nanosci. Nanotechnol., 2015, 15, 7980-7987.
[40]
Swami, M.B.; Jadhav, A.H.; Mathpati, S.R.; Ghuge, H.G.; Patil, S.G. Res. Chem. Intermed., 2016, 1164, 2745-2753.
[41]
Mohammadizadeh, M.R.; Taghavi, S.Z. E-J. Chem., 2011, 8, 101-106.
[42]
Zhang, M.; Li, Y.Q. Synth. Commun., 2006, 36, 835-841.
[43]
Ramineni, S.; Kannasani, R.K.; Peruri, V.V.S. Green Sustain. Chem, 2014, 4, 33-37.
[44]
Mahire, V.N.; Mahulikar, P.P. Chin. Chem. Lett., 2015, 26, 983-987.

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