Document Type: Original Research Article

Authors

1 Department of Chemistry , K. N. Toosi University of Technology, P.O. Box 15875-4416 Tehran, Iran

2 Organisch-Chemisches Institut der Universitaet Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany

10.33945/SAMI/AJGC/2020.1.5

Abstract

In this research article, we report the synthesis of imidazo[1,2-a]pyridine derivatives through Ugi condensation in the presence of saccharin as an organocatalyst used in a three component reaction. The convenient synthetic protocol, short reaction times, easy work up, good to excellent yields and mild reaction conditions make this process both practical and attractive.

Graphical Abstract

Keywords

Main Subjects

[1]. Jose G., Kumara T.H.S., Nagendrappa G., Sowmya H.B.V., Jasinski J.P., Millikan S.P., Chandrika N., More S.S., Harish B.G. Eur. J. Med. Chem., 2014, 77:288

[2]. Liu C., Chen Q., Yang M., Schneller S.W. Bioorg. Med. Chem., 2013, 21:359

[3]. Oslob J.D., Johnson R.J., Cai H., Feng S.Q., Hu L., Kosaka Y., Lai J., Sivaraja M., Tep S., Yang H., Zaharia C.A., Evanchik M.J., McDowell R.S. ACS Med. Chem. Lett., 2013, 4:113

[4]. Grädler U., Fuch T., Ulrich W.R., Boer R., Strub A., Hesslinger C., Anézo C., Diederichs K., Zaliani A. Bioorg. Med. Chem. Lett., 2011, 21:4228

[5]. Zhu Q., Wanga X., Chu Z., He G., Dong G., Xu Y. Bioorg. Med. Chem. Lett., 2013, 23:1993

[6]. Bavetsias V., Faisal A., Crumpler S., Brown N., Kosmopoulou M., Joshi A., Atrash B., Pérez-Fuertes Y., Schmitt J.A., Boxall K.J., Burke R., Sun C., Avery S., Bush K., Henley A., Raynaud F.I., Workman P., Bayliss R., Linardopoulos S., Blagg J. J. Med. Chem., 2013, 56:9122

[7]. Kumar Bagdi A., Santra S., Monir K., Hajra A. Chem. Commun., 2015, 51:1555

[8]. Moraski G.C., Markley L.D., Chang M., Cho S., Franzblau S.G., Hwang C.H., Boshoff H., Miller M.J. Bioorg. Med. Chem., 2012, 20:2214

[9]. Humphries A.C., Gancia E., Gilligan M.T., Goodacre, Hallett D., Marchant K.J., Thomas S.R. Bioorg. Med. Chem. Lett., 2006, 16:1518

[10]. Fookes C.J.R., Pham T.Q., Mattner F., Greguric I., Loch C., Liu X., Berghofer P., Shepherd R., Gregoire M.C., Katsifis A. J. Med. Chem., 2008, 51:3700

[11]. Chang L., Lee S.Y., Leonczak P., Rozenski J., De Jonghe S., Hanck T., Mȕller C.E., Herdewijn P. J. Med. Chem., 2014, 57:10080

[12]. Langer S.Z., Arbilla S., Benavides J., Scatton B. Adv. Biochem. Psychopharmacol., 1990, 46:61

[13]. Mizushige K., Ueda T., Yukiiri K., Suzuki H., Cardiovasc. Drug Rev., 2002, 20:163

[14]. Almirante L., Polo L., Mugnaini A., Provinciali E., Rugarli P., Biancotti A., Gamba A., Murmann W. J. Med. Chem., 1965, 8:305

[15]. Gudmundsson K., Johns B.A. Imidazo[1,2-a]pyridine derivatives for treatment of herpes viral infections, United States Patent Application, 2005, US20060167252

[16]. Koo H.L., Dupont H.L. Curr. Opin. Gastroenterol. 2010, 26:17

[17]. Li Ch., Chen L., Steinhuebel D., Goodman A. Tetrahedron Lett., 2016, 57:2708

[18]. Gao M., Wang M., Zheng Q.H. Bioorg. Med. Chem. Lett., 2016, 26:1371

[19]. Yang Y., Zhang Y., Yang L.Y., Zhao L., Si L., Zhang H., Liu Q., Zhou J.  Bioorg. Chem., 2017, 70:126

[20]. Waseem M.A., Rahila Ibad A., Ibad F., Neha S., Nazaan J., Saquib M., Siddiqui I.R., J. Heterocycl. Chem., 2017, 54:1094

[21]. Yu J., Jin Y., Zhang H., Yang X., Fu H. Chem. Eur. J., 2013, 19:16804

[22]. Chen C.J., Bando K., Ashino H., Taguchi K., Shiraishi H., Fujimoto O., Kitamura C., Matsushima S., Fujinaga M., Zhang M.R., Kasahara H., Minamizawa T., Jiang C., Ono M., Higuchi M., Suhara T., Yamada K., Ji B. Bioorg. Med. Chem., 2014, 22:4189

[23]. Terao Y., Suzuki H., Yoshikawa M., Yashiro H., Takekawa S., Fujitani Y., Okada K., Inoue Y., Yamamoto Y., Nakagawa H., Yao S., Kawamoto T., Uchikawa O. Bioorg. Med. Chem. Lett., 2012, 22:7326

[24]. Newhouse B.J., Wenglowsky S., Grina J., Laird E.R., Voegtli W.C., Ren L., Ahrendt K., Buckmelter A., Gloor S.L., Klopfenstein N., Rudolph J., Wen Z., Li X., Feng B. Bioorg. Med. Chem. Lett., 2013, 23:5896

[25]. Wang J., Dyers L., Mason R., Amoyaw P., Bu X.R. J. Org. Chem., 2005, 70:2353

[26]. Li G.Y., Jung K.H., Lee H., Son M.K., Seo J., Hong S.W., Jeong Y., Hong S., Hong S.S. Cancer Lett., 2013, 329:59

[27]. Rousseau A.L., Matlaba P., Parkinson C.J. Tetrahedron Lett., 2007, 48:4079

[28]. Adib M., Mahdavi M., Noghani M.A., Mirzaei P. Tetrahedron Lett., 2007, 48:7263

[29]. Püsküllü M.O., Karaaslan C., Bakar F., Göker H. Chem. Heterocycl. Compd., 2015, 51:723

[30]. Ramesha A.B., Raghavendra G.M., Nandeesh K.N., Rangappa K.S., Mantelingu K., Tetrahedron Lett., 2013, 54:95

[31]. Adib M., Mahdavi M., Abbasi A., Jahromi A.H., Bijanzadeh H.R. Tetrahedron Lett., 2007, 48:3217

[32]. Parenty A.D.C., Cronin L. Synthesis, 2008, 9:1479

[33]. Koubachi J., Berteina-Raboin S., Mouaddib A., Guillaumet G. Synthesis, 2009, 2:271

[34]. Guchhait S.K., Madaan C. Org. Biomol. Chem., 2010, 8:3631

[35]. Shaabani A., Soleimani E., Maleki A., Moghimi J. Synth. Commun., 2008, 38:1090

[36]. Zhu J., Bienaymé H., Multicomponent Reactions. In wiley, weinheim, 2005; p viii

[37]. Ramezanpour S., Bigdeli Z., Alavijeh N.S., Rominger F. Synlett., 2017, 28:1214