Web of Science (Emerging Sources Citation Index)

Document Type: Original Research Article

Authors

1 UNIVERSITY OF ZANJAN

2 University of Zanjan

3 Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran

10.33945/SAMI/ECC.2019.1.11

Abstract

Reactions of N-isocyaniminotriphenylphosphorane with a cyclic ketone in the presence of ferrocene carboxylic acid proceeded smoothly at room temperature and in neutral conditions to afford ferrocene-containing 1,3,4-oxadiazole derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, 1HNMR, and 13CNMR spectra. The method offers a mild, simple, and efficient route for the preparation oreaction of N-isocyaniminotriphenylphosphorane with cyclic ketones in the presence of ferrocene carboxylic acid proceeded smoothly at room temperature and in neutral conditions to afford ferrocene-containing 1,3,4-oxadiazole derivatives in high yields. The reaction proceeded smoothly and cleanly under mild conditions and no side reactions were observed. The structures of the products were deduced from their IR, 1HNMR, and 13CNMR spectra. f sterically congested ferrocene-containing 1,3,4-oxadiazole derivatives from cyclic ketones, N-isocyaniminotriphenylphosphorane (Ph3PNNC) and ferrocene carboxylic acid. Its ease of workup, high yields and fairy mild reaction conditions make it a useful addition to modern synthetic methodologies.

Graphical Abstract

Keywords

[1] A. Dömling, Chem. Rev., 2006, 106, 17-89.
 
[2] M. Passerini and L. Simone, Gazz. Chim. Ital., 1921, 51, 126-129.
 
[3] I. Ugi, Angew. Chem. Int. Ed., 1982, 21, 810-819.
 
[4] S. Scheibye, B. Pedersen and S.O. Lawesson, Bull. Soc. Chim. Belg., 1978, 87, 229-238.
 
[5] M. Alamgir, D.S.C. Black and N. Kumar, in Bioactive Heterocycles III, Springer, 2007, pp. 87-118.
 
[6] C. Gil and S. Bräse, J. Comb. Chem., 2008, 11, 175-197.
 
[7] F. Palacios, D. Aparicio, G. Rubiales, C. Alonso and J. M. de los Santos, Curr. Org. Chem., 2009, 13, 810-828.
 
[8] G. Hajos, I. Nagy, Curr. Org. Chem., 2008, 12, 39-58.
 
[9] D. Cobridge, Studies in Inorganic Chemistry, 1995, 20.
 
[10] H. Stolzenberg, B. Weinberger, W.P. Fehlhammer, F.G. Pühlhofer and R. Weiss, Eur. J. Inorg. Chem., 2005, 2005, 4263-4271.
 
[11] P. Molina, C. Conesa, A. Alías, A. Arques, M.D. Velasco, A.L. Llamas-Saiz, C. Foces-Foces, Tetrahedron, 1993, 49, 7599-7612.
 
[12] P. Molina, M.J. Vilaplana, Synthesis, 1994, 1994, 1197-1218.
 
[13] F. Palacios, C. Alonso and G. Rubiales, The Journal of Organic Chemistry, 1997, 62, 1146-1154.
 
[14] A. Souldozi, A. Ramazani, N. Bouslimani, R. Welter, Tetrahedron Lett., 2007, 48, 2617-2620.
 
[15] A. Ramazani and A. Rezaei, Org. Lett., 2010, 12, 2852-2855.
 
[16] A. Almasirad, S.A. Tabatabai, M. Faizi, A. Kebriaeezadeh, N. Mehrabi, A. Dalvandi, A. Shafiee, Bioorg. Med. Chem. Lett., 2004, 14, 6057-6059.
 
[17] M.D. Mullican, M.W. Wilson, D.T. Conner, C.R. Kostlan, D.J. Schrier, R.D. Dyer, J. Med. Chem., 1993, 36, 1090-1099.
 
[18] Ş.G. Küçükgüzel, E.E. Oruç, S. Rollas, F. Şahin, A. Özbek, Eur. J. Med. Chem., 2002, 37, 197-206.
 
[19] W.R. Tully, C.R. Gardner, R.J. Gillespie, R. Westwood, J. Med. Chem., 1991, 34, 2060-2067.
 
[20] C.-y. Chen, C.H. Senanayake, T. J. Bill, R.D. Larsen, T.R. Verhoeven, P.J. Reider, The Journal of Organic Chemistry, 1994, 59, 3738-3741.
 
[21] B.S. Holla, R. Gonsalves, S. Shenoy, Eur. J. Med. Chem., 2000, 35, 267-271.
 
[22] M.J. Crimmin, P.J. O'Hanlon, N.H. Rogers, G. Walker, J. Chem. Soc., Perkin Trans. 1, 1989, 2047-2057.
 
[23] U. Laddi, S. Desai, R. Bennur, S. Bennur, Indian J. Heterocycl. Chem., 2002, 11, 319-322.
 
[24] S.J. Dolman, F. Gosselin, P.D. O'Shea, I.W. Davies, The Journal of organic chemistry, 2006, 71, 9548-9551.
 
[25] E. Palaska, G. Şahin, P. Kelicen, N.T. Durlu, G. Altinok, Il Farmaco, 2002, 57, 101-107.
 
[26] I.R. Baxendale, S.V. Ley, M. Martinelli, Tetrahedron, 2005, 61, 5323-5349.
 
[27] S. Liras, M.P. Allen, B.E. Segelstein, Synth. Commun., 2000, 30, 437-443.
 
[28] V.K. Tandon, R.B. Chhor, Synth. Commun., 2001, 31, 1727-1732.
 
[29] S.H. Mashraqui, S.G. Ghadigaonkar, R.S. Kenny, Synth. Commun., 2003, 33, 2541-2545.
 
[30] F. Bentiss, M. Lagrenée, D. Barbry, Synth. Commun., 2001, 31, 935-938.
 
[31] E. Jedlovská, J. Leško, Synth. Commun., 1994, 24, 1879-1885.
 
[32] A. Souldozi, A. Ramazani, Tetrahedron Lett., 2007, 48, 1549-1551.
 
[33] I. Turel, Journal, 2015.
 
[34] S.A. Miller, J.A. Tebboth, J.F. Tremaine, Journal of the Chemical Society (Resumed), 1952, 632-635.
 
[35] K.E. Dombrowski, W. Baldwin, J.E. Sheats, J. Organomet. Chem., 1986, 302, 281-306.
 
[36] D.R. Van Staveren, N. Metzler-Nolte, Chem. Rev., 2004, 104, 5931-5986.
 
[37] C.S. Allardyce, A. Dorcier, C. Scolaro, P.J. Dyson, Appl. Organomet. Chem., 2005, 19, 1-10.
 
[38] G. Gasser, I. Ott, N. Metzler-Nolte, J. Med. Chem., 2010, 54, 3-25.
 
[39] C. Biot, N. François, L. Maciejewski, J. Brocard, D. Poulain, Bioorg. Med. Chem. Lett., 2000, 10, 839-841.
 
[40] P. Meunier, I. Ouattara, B. Gautheron, J. Tirouflet, D. Camboli and J. BESANCON, ChemInform, 1991, 22.
 
[41] W.C. Duivenvoorden, Y.-n. Liu, G. Schatte, H.-B. Kraatz, Inorg. Chim. Acta, 2005, 358, 3183-3189.
 
[42] C. Baldoli, S. Maiorana, E. Licandro, G. Zinzalla, D. Perdicchia, Org. Lett., 2002, 4, 4341-4344.
 
[43] G. Wilkinson, Organic Syntheses, 1956, 31-31.
 
[44] T. Kealy, P. Pauson, Nature, 1951, 168, 1039-1040.
[45] A. Ramazani, N. Fattahi, M. Ashtari, A. Rezaei, S. W. Joo, Phosphorus, Sulfur, and Silicon and the Related Elements, 2016, 191, 908-912.
 
[46] M. Ashtary, A. Ramazani, A. Kazemizadeh, N. Shajari, N. Fattahi, S.W. Joo, Phosphorus, Sulfur, and Silicon and the Related Elements, 2016, 191, 1402-1407.
 
[47] M.V. Holagh, A.M. O. MAHARRAMV, M.A. O. Allahverdiyev, A. Ramazani, Y. Ahmadi, A. Souldozi, Turkish Journal of Chemistry, 2012, 36, 179-188.
 
[48] A. Ramazani, N. Shajari, A.T. Mahyari, M. Khoobi, Y. Ahmadi, A. Souldozi, Phosphorus, Sulfur, and Silicon, 2010, 185, 2496-2502.
 
[49] A. Ramazani, F.Z. Nasrabadi, A. M. Malekzadeh, Y. Ahmadi, Monatshefte für Chemie-Chemical Monthly, 2011, 142, 625.
 
[50] M. Rouhani, A. Ramazani, S. W. Joo, Ultrason. Sonochem., 2015, 22, 391-396.
 
[51] A. Jafari, A. Ramazani, F. Sadri, S.W. Joo, Phosphorus, Sulfur, and Silicon and the Related Elements, 2016, 191, 316-321.