Copper(I) Iodide Supported Synthesis of Coumarin- and Quinolone-Annulated 2-Aminothiazoles

Abstract

An efficient and convenient method for the synthesis of coumarin- and quinolone-annulated 2-aminothiazoles is reported. The fused ring 2-aminothiazoles were synthesized from substituted coumarin/quinoline and phenylisothiocyanates in the presence of CuI, DABCO, and 1,10-phenanthroline. Both the rings in coumarin moiety supported the annulation by this method.

Key words

catalysis - fused-ring systems - quinolones - tandem - copper iodide

• References and Notes

• 1 Massari S, Daelemans D, Barreca ML, Knezevich A, Sabatini S, Cecchetti V, Marcello A, Pannecouque C, Tabarrini O. J. Med. Chem. 2010; 53: 641
• 2 Jimonet P, Audiau F, Barreau M, Blanchard JC, Boireau A, Bour Y, Coleno MA, Doble A, Doerflinger G, Do Huu C, Donat MH, Duchesne JM, Ganil P, Gueremy C, Honore E, Just B, Kerphirique R, Gontier S, Hubert P, Laduron PM, Blevec JL, Meunier M, Miquet JM, Nemecek C, Pasquet M, Piot O, Pratt J, Rataud J, Reibaud M, Stutzmann JM, Mignani S. J. Med. Chem. 1999; 42: 2828
• 3 Van Heusden J, Van Ginckel R, Bruwiere H, Moelans P, Janssen B, Floren W, Van der Leede BJ, Van Dun J, Sanz G, Venet M, Dillen L, Van Hove C, Willemsens G, Janicot M, Wouters W. Br. J. Cancer 2002; 86: 605
• 4 Gomaa MS, Armstrong JL, Bobillon B, Veal GJ, Brancale A, Redfern CP. F, Simons C. Bioorg. Med. Chem. 2008; 16: 8301
• 5a Kling A, Backfisch G, Delzer J, Geneste H, Graef C, Hornberger W, Lange U, Lauterbach A, Seitz W, Subkowski T. Bioorg. Med. Chem. 2003; 11: 1319
• 5b Liu C, Lin J, Pitt S, Zhang RF, Sack JS, Kiefer SE, Kish K, Doweyko AM, Zhang H, Marathe PH, Trzaskos J, Mckinnon M, Dodd JH, Barrish JC, Schieven GL, Leftheris K. Bioorg. Med. Chem. Lett. 2008; 18: 1874
• 5c Takagi K. Chem. Lett. 1986; 15: 265
• 6a Wipf P, Venkatraman S. J. Org. Chem. 1996; 61: 8004
• 6b Wang Y, Zhang W.-X, Wang Z, Xi Z. Angew. Chem. Int. Ed. 2011; 50: 8122
• 6c Wang Y, Zhao F, Chi Y, Zhang W.-X, Xi Z. J. Org. Chem. 2014; 79: 11146
• 7a Kalkhambkar RG, Kulkarni GM, Shivkumar H, Rao RN. Eur. J. Med. Chem. 2007; 42: 1272
• 7b Azam F, Alkskas IA, Khokra SL, Prakash O. Eur. J. Med. Chem. 2009; 44: 203
• 8a Alaimo RJ. J. Heterocycl. Chem. 1971; 8: 309
• 8b Lin AJ, Kasina S. J. Heterocycl. Chem. 1981; 18: 759
• 8c Dogruer DS, Unlu S, Sahin MF, Yesilada E. Farmaco 1998; 53: 80
• 8d Lopez-Calahorra F, Martinez-Rubio M, Velasco D, Brillas E, Julia L. Tetrahedron 2004; 60: 285
• 9 Joyce LL, Evindara G, Batey RA. Chem. Commun. 2004; 446
• 10a Guo Y, Tang R.-Y, Zhong P, Li J.-H. Tetrahedron Lett. 2010; 51: 649
• 10b Ding Q, Cao B, Liu X, Zong Z, Peng Y.-Y. Green Chem. 2010; 12: 1607
• 11 Majumdar KC, De N, Ghosh D, Ponra S, Roy B. Synthesis 2012; 44: 87
• 12 Anwar S, Paul SB, Majumdar KC, Choudhury S. Synth. Commun. 2014; 44: 3304
• 13a Wang JK, Peng F, Jiang J.-L, Lu ZJ, Wang LY, Bai JF, Pan Y. Tetrahedron Lett. 2008; 49: 467
• 13b Ding Q, He X, Wu J. J. Comb. Chem. 2009; 11: 587
• 13c Jones GO, Liu P, Houk KN, Buchwald SL. J. Am. Chem. Soc. 2010; 132: 6205
• 14 Baelen GV, Lemière GL. F, Dommisse RA, Maes BU. W. ARKIVOC 2009; (vi): 174
• 15 Analytical Data 2-(Phenylamino)-7H-chromeno[6,5-d]thiazol-7-one (2a) Pale yellow solid; mp 260–262 °C; yield: 70%. IR: 1540, 1617, 1722, 2862, 3245 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 6.40 (d, J = 9.6 Hz, 1 H), 7.27 (d, J = 7.6 Hz, 1 H), 7.40 (d, J = 7.2 Hz, 2 H), 7.45 (d, J = 7.2 Hz, 1 H), 7.51–7.57 (m, 3 H), 7.71 (d, J = 8.8, 1 H), 10.46 (br s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 112.35, 114.89, 116.55, 122.14, 127.90, 128.45, 128.51, 130.35, 140.86, 143.75, 149.54, 149.79, 160.73, 173.35: 6-Methyl-2-(phenylamino)thiazolo[5,4-f]quinolin-7(6H)-one (2d) Light brown solid; mp 288–290 °C; yield: 81%. IR: 1545, 1612, 1662, 2883, 3113 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 3.75 (s, 3 H), 6.69 (d, J = 9.2 Hz, 1 H), 7.31 (d, J = 8.8 Hz, 1 H), 7.40–7.45 (m, 3 H), 7.50–7.54 (m, 3 H), 7.77 (d, J = 9.2 Hz, 1 H), 10.24 (br s, 1 H). ¹³C NMR (100 MHz, CDCl₃): δ = 29.84, 112.66, 114.33, 121.57, 121.98, 127.87, 128.33, 129.49, 130.28, 135.51, 135.85, 143.94, 148.24, 161.80, 169.01. 2-(Phenylamino)-4H-chromeno[3,4-d]thiazol-4-one (2f) Off-white solid; mp > 300 °C; yield: 64%. IR: 1541, 1616, 1722, 2850, 3109 cm^–1. ¹H NMR (400 MHz, CDCl₃): δ = 7.18–7.24 (m, 2 H), 7.37–7.40 (m, 4 H), 7.46 (t, J = 7.6 Hz, 1 H), 7.54 (t, J = 7.6 Hz, 2 H), 10.22 (br s, 1 H).