Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, Tehran, P.O. Box 19395-4697, Yazd, Iran

2 Nano Structured Coatings Institute, Yazd Payame Noor University, Yazd, Iran

10.33945/SAMI/AJGC.2020.3.1

Abstract

An efficient and eco-friendly method for the synthesis of benzimidazole derivatives through the one-pot cyclocondensation of the substituted aldehydes with o-phenylenediamines over zinc sulfide nanoparticles (nano-ZnS) in ethanol as solvent at 70 °C has been described. The present method has several advantages such as high yields, easy purification, mild reaction conditions, easy work-up and short reaction times. The nanoparticles are easily synthesized, cheap, air and moisture stable, and also heterogenic and green catalysts.

Graphical Abstract

Keywords

[1]. a) Bhattacharya S., Chaudhuri P. Curr. Med. Chem., 2008, 15:1762; b) Horton D.A., Bourne G.T., Smythe M.L. Chem. Rev., 2003, 103:893; c) Boiani M., Gonzalez M. Mini-Rev. Med. Chem., 2005, 5:409

[2]. a) Bansal Y., Silakari O. Bioorg. Med. Chem., 2012, 20:6208;b) Fang X.J., Jeyakkumar P., Avula S.R., Zhou C.H. Bioorg. Med. Chem. Lett., 2016, 26:2584; c) Kamal A., Rao M.P.N., Swapna P., Srinivasulu V., Bagul C., Shaik A.B., Mullagiri K., Kovvuri J., Reddy V.S., Vidyasagar K., Nagesh N. Org. Biomol. Chem., 2014, 12:2370

[3]. a) Preston P.N., Stevens M.F.G,. Tennant G. Benzimidazoles and Congeneric Tricyclic Compounds, Part 2, John Wiley and Sons New York., 1980; b) Cedillo-River R., Munaz O. J. Med. Microbiol., 1992, 37:221; c) Chavez B., Cedillo-Rivera R., Martiner-Palomo A. J. Protozool., 1992, 39:510; d) Navarrete-Vazquez G., Cedillo R., Hernandez-Campos A., Yepez L., Hernandez-Luis F., Valdez J., Morales R., Cortes R., Hernandez M., Castillo R. Bioorg. Med. Chem. Lett., 2001, 11:187

[4]. a) Hernandez-luis F., Hernandez-Campos A., Castillo R., Navarrete-Vazquez G., Soria-Arteche O., Hernandez-Hernandez M., Mulia Y.L. Eur. J. Med. Chem., 2010, 45:3135; b) Khalil A.M., Berghot M.A., Gouda M.A. Eur. J. Med. Chem., 2010, 45:1552

[5]. a) Kamal A., Ponnampalli S., Vishnuvardhan M.V.P.S., Rao M.P.N, Mullagiri K., Nayak V.L., chandrakant B. Med. Chem. Comm., 2014, 5:1644; b) Saour K., Lafta D. Med. Chem., 2016, 16:891; c) Kim M.K., Shin H., park K., Kim H., park J., Kim K., Nam J., Choo H., Chong Y. J. Med. Chem., 2015, 58;7596

[6]. Chassaing C., Berger M., Heckeroth A., Ilg T., Jaeger M., Kern C., Schmid K., Uphoff M. J. Med. Chem., 2008, 51:1111

[7]. Wang J.L., Zhang J., Zhou Z.M., Li Z.H., Xue W.Z., Xu D., Hao L.P., Han X.F., Fei F., Liu T., Liang A.H. J. Med. Chem., 2012, 49:183

[8]. a) Mavrova A.T., Yancheva D., Anastassova N., Anichina K., Zvezdanovic J., Djordjevic A., Markovic D., Smelcerovic A. Bioorg. Med. Chem., 2015, 23:6317; b) Holloway G.A., Baell J.B., Fairlamb A.H., Novello P.M., Parisot J.P., Richardson J., Watson K.G., Street I.P. Bioorg. Med. Chem. Lett., 2007, 17:1422

[9]. a) Hameed P.S., Raichurkar A., Madhavapeddi P., Menasinakai S., Sharma S., Kaur P., Nandishaiah R., Panduga V., Reddy J., Sambandamurthy V.K., Sriram D. ACS Med. Chem. Lett., 2014, 5:820; b) Park B., Awasthi D., Chowdhury S.R., Melief E.H., Kumar K., Knudson S.E., Slayden R.A., Ojima I. Bioorg. Med. Chem., 2014, 22:2602

[10]. Mader M., Dedios A., Shih C., Bonjouklian R., Li T., White W., Uralde B.L., Martinez C.S., Prado M., Jaramillo C., Diego E., Cabrejas M., Dominguez L.M., Mantero C., Shephered T., Dally R., Toth J.E., Chatterjee A., Pleite S., Blanco-Urgoiti J., Perez L., Barberis M., Lorite M.J., Jambrina E., Nevill J.C.R., Lee P.A., SchuLtz R.C., Wolos J.A., Li L.C., Campbell R.M., Anderson B.D. Bioorg. Med. Chem. Lett., 2008, 18:179

[11]. Skinner-Adams T.S., Davis T.M.E., Manning L.S., Johnston W.A. Trans R. Soc. Trop. Med. Hyg., 1997, 91:580

[12]. Palmer B.D., Kraker A.J., Hartl B.G., Panopoulos A.D., Panek R.L., Batley B.L., Lu G.H., Trumpp-Kallmeyer S., Showalter H.D., Denny W.A. J. Med. Chem., 1999, 42:2373

[13]. Barker H.A., Smyth R.D., Weissbach H., Toohy J.I., Ladd J.N., Volcani B.E. J. Biol. Chem., 1960, 235:480

[14]. a) Kuhler T.C., Swanson M., Shcherbuchin V., Larsson H., Mellgard B., Jostrom J.E. J. Med. Chem., 1998, 41:1777; b) Richter J.E. Am. J. Gastroentreol., 1997, 92:30

[15]. a) Mavrova A., Anichina K.K., Vucher D.I., Tsenov J.A., Denkova P.S., Kondeva M.S., Micheva M.K. Eur. J. Med. Chem., 2006, 41:1412; b) Andrews P., Dorn H., Voege H. US Patent 5036069

[16]. Jeshma K., Nagaraju B., Kamal A., Ajay K.S. ACS Comb. Sci., 2016, 18:644

[17]. Sharghi H., Asemani O., Tabaei S.M.H. Chem. Susc., 2008, 45:1293

[18]. Kathirvelan D., Yuvaraj P., Babu K., Nagarajan A.S., Reddy B.S.R. Indian J. Chem. B, 2013, 52:1152

[19]. Kedar M.S., Dighe N.S., Pattan S.H.R., Musmade D.S., Dipak T., Bhosale M., Gaware V.M. Der Pharma Chem., 2010, 2:249

[20]. a) zhang Z.H., Yin L., Wang Y.M. Catal. Commun., 2007, 8:1126; b) Kommi D.N., Kumar D., Bansal R., Chebolu R., Chakraborti A.K. Green Chem., 2012, 14:3329; c) Bressi J.C., Jong R.D., Wu Y., Jennings A.J., Brown J.W., Connell O.S., Tari L.W., Skene R.J., Vu P., Naver M., Cao X., Gangloff A.R. Bioorg. Med. Chem. Lett., 2010, 20:3138

[21]. a) Baars H., Beyer A., Kohlhepp S.V., Bolm C. Org. Lett., 2014, 16:536; b) Sluiter J., Christoffers J. Synlett, 2009, 63; c) Saha P., Ramana T., Purkait N., Ali M.A., Paul R., Punniyamurthy T. J. Org. Chem., 2009, 74:8719

[22]. a) Mahesh D., Sadhu P., Punniyamurthy T. J. Org. Chem., 2015, 80:1644; b) Blacker A.J., Farah M.M., Hall M.I., Marsden S.P., Saidi O., Williams J.M.J. Org. Lett.,2009, 11:2039

[23]. a) Dudd L.M., Venardou E., Garcia-Verdugo E., Licence P., Blake A.J., Wilson C., Poliakoff M. Green Chem., 2003, 5:187; b) Rambabu D., Murthi P.R.K., Dulla B., Rao B.M.V., Pal M. Synth. Commun., 43:3083

[25]. a) Salehi P., Dabiri M., Zolfigol M.A., Otokesh S., Baghbanzadeh M. Tetrahedron Lett., 2006, 47:2557; b) Chebolu R., Kommi D.N., Kumar D., Bollineni N., Chakraborti A.K. J. Org. Chem., 2012, 77:10158

[26]. Rathore K.S., Patidar D., Janu Y., Saxena K., Sharma K., Sharma T.P. Chalcogenide Lett., 2008, 5:105

[27]. Wang C., Li Q., Hu B. Chin. Opt. Lett., 2009, 7:432