Water-Mediated Green Synthesis of Benzimidazoles Using Pyruvic Acid: A
Comparable Study of Ultra-sonication versus Conventional Heating

Santosh    Rangnath    Deshmukh; Archana    Subhash    Nalkar; Shankar    Ramchandra    Thopate

Abstract

An efficient and green protocol has been introduced for the synthesis of benzimidazole derivatives using a pyruvic acid catalyst in the presence of water. Pyruvic acid catalyses the reaction of aromatic aldehydes with o-phenylenediamine efficiently, and products were obtained in good to excellent yields under sonication (50 °C) or under conventional heating (50 °C). The advantages of this synthetic methodology are the use of eco-friendly, commercially cheap, biodegradable catalyst, metal-free and Lewis acid-free mild reaction conditions with excellent yields, short reaction times, and compatible with a wide range of electronically diverse substrates. Pyruvic acid in water as a catalyst under ultrasound irradiation can be a better alternative to synthesize benzimidazole derivatives than some of the traditional methods.

Keywords: Pyruvic acid, benzimidazole, aldehyde, o-phenylenediamine, ultrasound irradiation, green chemistry, heterocyclic chemistry.

Graphical Abstract

[1] 
Amari, M.; Fodili, M.; Nedja-Kolli, B.; Hoffmann, A.P.; Perie, J. J. Heterocycl. Chem.,  2002, 39(4), 811-816.
[http://dx.doi.org/10.1002/jhet.5570390429] 
[2] 
McClellan, K.J.; Markham, A. Telmisartan. Drugs,  1998, 56(6), 1039-1044.
[http://dx.doi.org/10.2165/00003495-199856060-00007] [PMID:  9878991] 
[3] 
Srinivasulu, R.; Kumar, K.R.; Satyanarayana, P.V.V. Green Sustain. Chem,  2014, 4, 33-37.
[http://dx.doi.org/10.4236/gsc.2014.41006] 
[4] 
Mostafavi, H.; Islami, M.R.; Ghonchepour, E.; Tikdari, A.M. Chem. Pap.,  2018, 72, 2973-2978.
[http://dx.doi.org/10.1007/s11696-018-0540-5] 
[5] 
Craft, T.M. Torsade de pointes after astemizole overdose. Br. Med. J. (Clin. Res. Ed.),  1986, 292(6521), 660.
[http://dx.doi.org/10.1136/bmj.292.6521.660] [PMID:  2868774] 
[6] 
Prajapat, P.; Kumawat, M.; Talesara, G.L.; Kalal, P.; Agarwal, S.; Kapoor, C.S. J. Chem. Biol. Interfaces.,  2018, 8, 1-10.
[7] 
Albanese, G.; Venturi, C.; Galbiati, G. Int. J. Dermatol.,  2001, 40(1), 67-71.
[http://dx.doi.org/10.1046/j.1365-4362.2001.01103.x] [PMID:  11277961] 
[8] 
Davila-Gutierrez, C.E.; Vasquez, C.; Trujillo-Hernandez, B.; Huerta, M. Am. J. Trop. Med. Hyg.,  2002, 66(3), 251-254.
[http://dx.doi.org/10.4269/ajtmh.2002.66.251] [PMID:  12139216] 
[9] 
Dhanalakshmi, P.; Thimmarayaperumal, S.; Shanmugam, S. RSC Advances,  2014, 4(23), 12028-12036.
[http://dx.doi.org/10.1039/C3RA47761D] 
[10] 
Crudden, C.M.; Horton, J.H.; Narouz, M.R.; Li, Z.; Smith, C.A.; Munro, K.; Baddeley, C.J.; Larrea, C.R.; Drevniok, B.; Thanabalasingam, B.; McLean, A.B.; Zenkina, O.V.; Ebralidze, I.I.; She, Z.; Kraatz, H.B.; Mosey, N.J.; Saunders, L.N.; Yagi, A. Nat. Commun.,  2016, 7, 12654.
[http://dx.doi.org/10.1038/ncomms12654] [PMID:  27585494] 
[11] 
Kang, S.; Park, S.; Kang, H.; Cho, S.J.; Song, H.; Yoon, H. J. Chem. Commun. (Camb.),  2019, 55(60), 8780-8783.
[http://dx.doi.org/10.1039/C9CC01585J] [PMID:  30931445] 
[12] 
Kang, S.; Byeon, S.E.; Yoon, H.J. Bull. Korean Chem. Soc.,  2021, 42, 712-723.
[http://dx.doi.org/10.1002/bkcs.12261] 
[13] 
Nagawade, R.R.; Shinde, D.B. Russ. J. Org. Chem.,  2006, 42, 453-454.
[http://dx.doi.org/10.1134/S1070428006030201] 
[14] 
Wang, L.; Sheng, J.; Tian, H.; Qian, C. Synth. Commun.,  2004, 34(23), 4265-4272.
[http://dx.doi.org/10.1081/SCC-200039340] 
[15] 
Nguyen, K.M.H.; Largeron, M. Chemistry,  2015, 21(36), 12606-12610.
[http://dx.doi.org/10.1002/chem.201502487] [PMID:  26206475] 
[16] 
Singh, M.P.; Sasmal, S.; Lu, W.; Chatterjee, M.N. Synthesis,  2000, 10, 1380-1390.
[http://dx.doi.org/10.1055/s-2000-7111] 
[17] 
Trivedi, R.; De, S.K.; Gibbs, R.A. J. Mol. Catal. A,  2006, 245(1), 8-11.
[http://dx.doi.org/10.1016/j.molcata.2005.09.025] 
[18] 
Zhang, Z.H.; Yin, L.; Wang, Y.M. Catal. Commun.,  2007, 8(7), 1126-1131.
[http://dx.doi.org/10.1016/j.catcom.2006.10.022] 
[19] 
Sharghi, H.; Aberi, M.; Doroodmand, M.M. Adv. Synth. Catal.,  2008, 350, 2380-2390.
[http://dx.doi.org/10.1002/adsc.200800317] 
[20] 
Khan, A.T.; Parvin, T.; Choudhury, L.H. Synth. Commun.,  2009, 39(13), 2339-2346.
[http://dx.doi.org/10.1080/00397910802654815] 
[21] 
Itoh, T.; Nagata, K.; Ishikawa, H.; Ohsawa, A. Heterocycles,  2004, 63, 2769-2783.
[http://dx.doi.org/10.3987/COM-04-10215] 
[22] 
Chari, M.A.; Sadanandam, P.; Shobha, D.; Mukkanti, K. J. Heterocycl. Chem.,  2010, 47(1), 153-155.
[23] 
Chari, M.A.; Shobha, D.; Sasaki, T. Tetrahedron Lett.,  2011, 52(43), 5575-5580.
[http://dx.doi.org/10.1016/j.tetlet.2011.08.047] 
[24] 
Ruiz, V.R.; Corma, A.; Sabater, M.J. Tetrahedron,  2010, 66(3), 730-735.
[http://dx.doi.org/10.1016/j.tet.2009.11.048] 
[25] 
Chari, M.A.; Shobha, D.; Kenawy, E.R.; Al-Deyab, S.S.; Reddy, B.V.S.; Vinu, A. Tetrahedron Lett.,  2010, 51(39), 5195-5199.
[http://dx.doi.org/10.1016/j.tetlet.2010.07.132] 
[26] 
Cano, N.H.; Uranga, J.G.; Nardi, M.; Procopio, A.; Wunderlin, D.A.; Santiago, A.N. Beilstein J. Org. Chem.,  2016, 12, 2410-2419.
[http://dx.doi.org/10.3762/bjoc.12.235] [PMID:  28144309] 
[27] 
Alinezhad, H.; Salehian, F.; Biparva, P. Synth. Commun.,  2010, 42, 102-108.
[http://dx.doi.org/10.1080/00397911.2010.522294] 
[28] 
Maiti, D.K.; Halder, S.; Pandit, P.; Chatterjee, N.; De Joarder, D.; Pramanik, N.; Saima, Y.; Patra, A.; Maiti, P.K. J. Org. Chem.,  2009, 74(21), 8086-8097.
[http://dx.doi.org/10.1021/jo901458k] [PMID:  19799443] 
[29] 
Gogoi, P.; Konwar, D. Tetrahedron Lett.,  2006, 47(1), 79-82.
[http://dx.doi.org/10.1016/j.tetlet.2005.10.134] 
[30] 
Du, L-H.; Wang, Y-G. Synthesis,  2007, 5, 675-678.
[31] 
Verner, E.; Katz, B.A.; Spencer, J.R.; Allen, D.; Hataye, J.; Hruzewicz, W.; Hui, H.C.; Kolesnikov, A.; Li, Y.; Luong, C.; Martelli, A.; Radika, K.; Rai, R.; She, M.; Shrader, W.; Sprengeler, P.A.; Trapp, S.; Wang, J.; Young, W.B.; Mackman, R.L. J. Med. Chem.,  2001, 44(17), 2753-2771.
[http://dx.doi.org/10.1021/jm0100638] [PMID:  11495587] 
[32] 
Lin, S.; Yang, L. Tetrahedron Lett.,  2005, 46(25), 4315-4319.
[http://dx.doi.org/10.1016/j.tetlet.2005.04.101] 
[33] 
Kakkar, D.; Tiwari, A.K.; Chuttani, K.; Khanna, A.; Datta, A.; Singh, H.; Mishra, A.K. Chem. Biol. Drug Des.,  2012, 80(2), 245-253.
[http://dx.doi.org/10.1111/j.1747-0285.2012.01394.x] [PMID:  22515497] 
[34] 
Saha, D.; Saha, A.; Ranu, B.C. Green Chem.,  2009, 11, 733-737.
[http://dx.doi.org/10.1039/b823543k] 
[35] 
Heravi, M.M.; Sadjadi, S.; Oskooie, H.A.; Shoar, R.H.; Bamoharram, F.F. Catal. Commun.,  2008, 9(4), 504-507.
[http://dx.doi.org/10.1016/j.catcom.2007.03.011] 
[36] 
Das, B.; Holla, H.; Srinivas, Y. Tetrahedron Lett.,  2007, 48(1), 61-64.
[http://dx.doi.org/10.1016/j.tetlet.2006.11.018] 
[37] 
Sharghi, H.; Asemani, O.; Tabaei, S.M.H. J. Heterocycl. Chem.,  2008, 45(5), 1293-1298.
[http://dx.doi.org/10.1002/jhet.5570450506] 
[38] 
Ma, H.; Wang, Y.; Wang, J. Heterocycles,  2006, 68(8), 1669-1673.
[http://dx.doi.org/10.3987/COM-06-10785] 
[39] 
Feizpour, F.; Jafarpour, M.; Rezaeifard, A. Catal. Lett.,  2018, 148, 30-40.
[http://dx.doi.org/10.1007/s10562-017-2232-0] 
[40] 
Wrobel, Z.; Stachowska, K. Grudzień K.; Kwast, A. Synlett,  2011, (10), 1439-1443.
[http://dx.doi.org/10.1055/s-0030-1260764] 
[41] 
Ibrahim, K.S.; Begum, J. Int. J. Pharma Sci.,  2011, 2, 298-302.
[42] 
Majumdar, S.; Chakraborty, M.; Pramanik, N.; Maiti, D.K. RSC Advances,  2015, 5(63), 51012-51018.
[http://dx.doi.org/10.1039/C5RA08183A] 
[43] 
Su, F.; Mathew, S.C.; Mohlmann, L.; Antonietti, M.; Wang, X.; Blechert, S. Angew. Chem.,  2011, 50(3), 657-660.
[http://dx.doi.org/10.1002/anie.201004365] 
[44] 
Kovvuri, J.; Nagaraju, B.; Kamal, A.; Srivastava, A.K. ACS Comb. Sci.,  2016, 18(10), 644-650.
[http://dx.doi.org/10.1021/acscombsci.6b00107] [PMID:  27631587] 
[45] 
Samanta, S.; Das, S.; Biswas, P. J. Org. Chem.,  2013, 78(22), 11184-11193.
[http://dx.doi.org/10.1021/jo401445j] [PMID:  24134516] 
[46] 
Yu, Z.Y.; Zhou, J.; Fang, Q.S.; Chen, L.; Song, Z.B. Chem. Pap.,  2016, 70(9), 1293-1298.
[http://dx.doi.org/10.1515/chempap-2016-0056] 
[47] 
Kathirvelan, D.; Yuvaraj, P.; Babu, K.; Nagarajan, A.S.; Reddy, B.S.R. Indian J. Chem.,  2013, 52B, 1152-1156.
[48] 
Shaikh, K.A.; Patil, V.A. Org. Commun.,  2012, 5, 12-17.
[49] 
Kidwai, M.; Jahan, A.; Bhatnagar, D. J. Chem. Sci.,  2010, 122, 607-612.
[http://dx.doi.org/10.1007/s12039-010-0095-7] 
[50] 
Karimi-Jaberi, Z.; Amiri, M. J. Chem.,  2012, 9(1), 167-170.
[51] 
Khunt, M.D.; Kotadiya, V.C.; Viradiya, D.J.; Baria, B.H.; Bhoya, U.C. Int. Lett. Chem. Phys. Astron.,  2014, 6, 61-68.
[http://dx.doi.org/10.18052/www.scipress.com/ILCPA.25.61] 
[52] 
Ryu, K.E.; Kim, B.R.; Sung, G.H.; Yoon, H.J.; Yoon, Y.J. Synlett,  2015, 26, 1985-1990.
[http://dx.doi.org/10.1055/s-0034-1378783] 
[53] 
Dudd, L.M.; Venardou, E.; Verdugo, E.G.; Licence, P.; Blake, A.J.; Wilson, C.; Poliakoff, M. Green Chem.,  2003, 5, 187-192.
[http://dx.doi.org/10.1039/b212394k] 
[54] 
Bayardon, J.; Holz, J.; Schaffner, B.; Andrushko, V.; Verevkin, S.; Preetz, A.; Borner, A. Angew. Chem. Int. Ed.,  2007, 46(31), 5971-5974.
[http://dx.doi.org/10.1002/anie.200700990] 
[55] 
Jessop, P.G. Green Chem.,  2011, 13, 1391-1398.
[http://dx.doi.org/10.1039/c0gc00797h] 
[56] 
Zhang, Z.; Song, J.; Han, B. Chem. Rev.,  2017, 117(10), 6834-6880.
[http://dx.doi.org/10.1021/acs.chemrev.6b00457] [PMID:  28535680] 
[57] 
Ray, S.; Manna, P.; Mukhopadhyay, C. Ultrason. Sonochem.,  2015, 22, 22-29.
[http://dx.doi.org/10.1016/j.ultsonch.2014.06.015] [PMID:  25023825] 
[58] 
Ashokkumar, M. Ultrason. Sonochem.,  2011, 18(4), 864-872.
[http://dx.doi.org/10.1016/j.ultsonch.2010.11.016] [PMID:  21172736] 
[59] 
Mason, T. J. Chem. Soc. Rev.,  1997, 26, 443-451.
[http://dx.doi.org/10.1039/cs9972600443] 
[60] 
Wang, S.F.; Guo, C.L.; Cui, K.K.; Zhu, Y.T.; Ding, J.X.; Zou, X.Y.; Li, Y.H. Ultrason. Sonochem.,  2015, 26, 81-86.
[http://dx.doi.org/10.1016/j.ultsonch.2015.01.002] [PMID:  25605585] 
[61] 
Maleki, B.; Baghayeri, M.; Abadi, S.A.J.; Tayebee, R.; Khojastehnezhad, A. RSC Advances,  2016, 6, 96644-96661.
[http://dx.doi.org/10.1039/C6RA20895A] 
[62] 
Jung, S.; Kim, S.Y.; Yoon, H.J. Synlett,  2020, 31, 1343-1348.
[http://dx.doi.org/10.1055/s-0040-1707145] 
[63] 
Jung, S.; Yoon, H.J. Angew. Chem. Int. Ed.,  2020, 59, 4883-4887.
[http://dx.doi.org/10.1002/anie.201915438] 
[64] 
Li, Y.; Chen, J.; Lun, S.Y. Appl. Microbiol. Biotechnol.,  2001, 57(4), 451-459.
[http://dx.doi.org/10.1007/s002530100804] [PMID:  11762589] 
[65] 
Stanko, R.T.; Tietze, D.L.; Arch, J.E. Am. J. Clin. Nutr.,  1992, 56(4), 630-635.
[http://dx.doi.org/10.1093/ajcn/56.4.630] [PMID:  1414961] 
[66] 
Stanko, R.T.; Reynolds, H.R.; Hoyson, R.; Janosky, J.E.; Wolf, R. Am. J. Clin. Nutr.,  1994, 59(2), 423-427.
[http://dx.doi.org/10.1093/ajcn/59.2.423] [PMID:  8310996] 
[67] 
Stanko, R.T.; Robertson, R.J.; Galbreath, R.W.; Reilly, J.J., Jr; Greenawalt, K.D.; Goss, F.L. J. Appl. Physiol.,  1990, 69(5), 1651-1656.
[http://dx.doi.org/10.1152/jappl.1990.69.5.1651] [PMID:  2272957] 
[68] 
DeBoer, L.W.; Bekx, P.A.; Han, L.; Steinke, L.J. Appl. Physio.,  1993, 265(5), 1571-1576.
[69] 
Borle, A.B.; Stanko, R.T. J. Appl. Physiol.,  1996, 270(3), 535-540.
[70] 
Heravi, M.R.P.; Ashori, M. J. Chem.,  2013, 1-5.

Cite As

Letters in Organic Chemistry

Water-Mediated Green Synthesis of Benzimidazoles Using Pyruvic Acid: A Comparable Study of Ultra-sonication versus Conventional Heating

Abstract

Graphical Abstract