Document Type: Original Research Article

Author

Department of Chemistry, College of Science, University of Mosul, Mosul, Iraq

10.33945/SAMI/AJGC/2020.2.2

Abstract

Hippuric hydrazones 4–8 were prepared starting from treating the corresponding acid with ethanolic HCl forming the corresponding ester 2. The formed ester was then converted to ethyl hippurate 3 by treating the ester with hydrazine hydrate. The formed ethyl hippurate was then irradiated with various substituted aromatic aldehydes under solvent-free conditions forming new series of hippuric hydrazones 4–8. Developing clean synthetic route for synthesizing hippuric hydrazones is the main point of this work which is environmentally and economically desirable. The synthesized compounds were confirmed by spectral NMR, mass, IR and CHN analysis data.

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[1]. Turan-Zitouni G., Blache Y., Güven K. Boll. Chim. Farm., 2001, 140:397

[2]. Peng G., Yunyang W. Heterocyclic Commun., 2013, 19:113

[3]. Samudranil P., Balavardhana Rao A.R. J. Organomet. Chem., 2013, 731:67

[4]. Chang J., Huang G., Liu H., Yu W., Zhang Y., Chang J., Dong L., Li Y., Yu X. J. Org. Chem., 2013,78:10337

[5]. Nun P., Martin C., Martinez J., Lamaty F. Tetrahedron, 2013, 67:8187

[6]. Hu Y., Lu X., Chen K., Yan R., Li Q.S., Zhu H.L. Bioorg. Med. Chem., 2012, 20:903

[7]. Tan K.L., Jacobsen E.N. Angew. Chem. Int. Edi., 2007,46:1315

[8]. Noulsri E., Richardson R., Lerdwana S., Fucharoen S., Yamagishi T., Kalinowski D.S., Pattanapanyasat K. Am. J. Hematol., 2009, 84:170

[9]. Chen K., Tan Z., He M., Li J., Tang S., Hewlett I., Yu F., Jin Y., Yang M. Chem. Biol. Drug Des., 2010, 76:25

[10]. Lu D., Giles K., Li Z., Satish R., Elena D. J. Pharmacol. Exp. Ther., 2013, 347:325

[11]. Andreani A., Burnelli S., Granaiola M., Leoni A., Locatelli A., Morigi R., Rambaldi M., Varoli L., Calonghi N., Cappadone C., Farruggia G., Zini M., Stefanelli C., Masotti L., Radin N.S., Shoemaker R.H.     J. Med. Chem., 2008, 51:809

[12]. Ramin H. J. Scientific Res., 2013, 13:1186

[13]. Yadav A.G., Patil V.N., Asrondkar A.L., Naik A.A., Ansulkar P.V. Rasayan J. Chem., 2012, 5:117

[14]. Zafer D., Asım K. Lett. Drug Des. Discovery, 2012,9:310

[15]. Sridhar S.K. Eur. J. Pharm. Sci., 2002,16:129

[16]. Stork G., Benaim J. Org. Synth., 1977, 6:242

[17]. Day A.C., Whiting M.C. Org. Synth., 1970, 6:10

[18]. Belskaya N.P., Dehaen W., Bakulev V.A. Arkivoc, 2010, 2010:275

[19]. Strappaghetti G., Brodi C., Giannaccini G. Bioorg. Med. Chem. Lett., 2006, 16:2575

[20]. Wu A.M., Senter P.D. Nat. Biotechnol., 2005, 23:1137

[21]. Katyal M., Dutt Y. Talanta, 1975, 22:151

[22]. Mohan M., Gupta M.P., Chandra L., Jha N.K. Inorg. Chim. Acta, 1988, 151:61

[23]. Sinh J. Talanta, 1982, 29:77

[24]. Molodykh V., Buzykin I., Bystrykn N., Kitaev P. Khim. Farm. Zh., 1978, 11:37

[25]. Hoffman M.R. Sci. Technol., 1994, 28:2080

[26]. Terra L.H.S.A., Areias M.C.C., Gaubeur I., Encarnación M., Suárez-iha V. Spectroscopy Lett., 1999, 32:257

[27]. Kulcsár G. Cancer Detect Prev., 2000, 24:485

[28]. Wiklund P., Bergman J. Curr. Org. Synth., 2006, 3:379

[29]. Krishnan H.K., Muni N.M., Sahruna N.S. J. Adv. Chem., 2014, 4:266