The Reaction of 2-(Acylamino)benzonitriles with Primary Aromatic Amines: A Convenient Synthesis of 2-Substituted 4-(Arylamino)quinazolines

Abstract

2-Substituted 4-(arylamino)quinazolines were prepared from 2-(acylamino)benzonitriles and primary arylamines by refluxing in either ethanol using trifluoroacetic acid as a catalyst or acetic acid. The 2-aminobenzonitrile was acylated by reaction with anhydrides, isocyanates, or ethyl chloroformate at room temperature.

Key words

acylation - cyclization - heterocycles - 4-aminoquinazolines - 2-aminobenzonitrile

• References

• 1 Yoon DS, Han Y, Stark TM, Haber JC, Gregg BT, Stankovich SB. Org. Lett. 2004; 6: 4775 ; and references therein
• 2 Connolly DJ, Cusack D, O’Sullivan TP, Guiry PJ. Tetrahedron 2005; 61: 10153
• 3 Khan I, Ibrar A, Abbas N, Saeed A. Eur. J. Med. Chem. 2014; 76: 193 ; and references therein
• 4a Garofalo A, Goossens L, Six P, Lemoine A, Ravez S, Farce A, Depreux P. Bioorg. Med. Chem. Lett. 2011; 21: 2106
• 4b Portela-Cubillo F, Scott JS, Walton JC. J. Org. Chem. 2009; 74: 4934
• 5 Li F, Feng Y, Meng Q, Li W, Li Z, Wang Q, Tao F. ARKIVOC 2007; (i): 40
• 6a Foucourt A, Bernard-Dubouilh C, Chosson E, Corbière C, Buquet C, Iannelli M, Leblond B, Marsais F, Besson T. Tetrahedron 2010; 66: 4495 ; and references therein
• 6b Sirisoma N, Pervin A, Zhang H, Jiang S, Willardsen JA, Anderson MB, Mather G, Pleiman CM, Kasibhartla S, Tseng B, Drewe J, Cai SX. J. Med. Chem. 2009; 52: 2341
• 7 Tsou H, Mamuya N, Johnson BD, Reich MF, Gruber BC, Ye F, Nilakantan R, Shen R, Discafani C, DeBlanc R, Davis R, Koehn FE, Greenberger LM, Wang Y, Wissner A. J. Med. Chem. 2001; 44: 2719
• 8 Hamed MM, Abou El Ella DA, Keeton AB, Piazza GA, Engel M, Hartmann RW, Abadi AH. Med. Chem. Commun. 2013; 4: 1202
• 9 Wang Z, Wang C, Sun Y, Zhang N, Liu Z, Liu J. Tetrahedron 2014; 70: 906
• 10a Shen Z, Hong Y, He X, Mo W, Hu B, Sun N, Hu X. Org. Lett. 2010; 12: 552
• 10b Shreder KR, Wong MS, Nomanbhoy T, Leventhal PS, Fuller SR. Org. Lett. 2004; 6: 3715
• 10c Scarborough HC, Lawers BC, Mikielli JL, Compton JL. J. Org. Chem. 1962; 27: 957
• 11 Kurteva VB, Zlatanova VN, Dimitrov VD. ARKIVOC 2006; (i): 46
• 12 Mederski W, Devant R, Barnickel G, Bernotat-Danielowski S, Vickers J, Cezanne B, Dhanoa D, Zhao B.-P, Rinker J, Player MR, Jaegar E, Soll R. WO 2002024667 A1, 2002
• 13 Kim SH, Kim SH, Kim TH, Kim JN. Tetrahedron Lett. 2010; 51: 2774
• 14 Sharghi H, Jokar M, Doroodmand MM. Adv. Synth. Catal. 2011; 353: 426
• 15 Wu X.-F, Oschatz S, Sharif M, Beller M, Langer P. Tetrahedron 2014; 70: 23
• 16 Gelotte KO, Mason DN, Meckler H, Shieh W.-C, Starkey CM. J. Heterocycl. Chem. 1990; 27: 1549
• 17 Szczepankiewicz W, Suwinski J. J. Chem. Heterocycl. Compd. 2000; 36: 809
• 18 Marinho E, Araújo R, Proença F. Tetrahedron 2010; 66: 8681 ; and references therein
• 19 Xue S, McKenna J, Shieh W.-C, Repic O. J. Org. Chem. 2004; 69: 6474
• 20 Liu X, Fu H, Jiang Y, Zhao Y. Angew. Chem. Int. Ed. 2009; 48: 348