Synthesis of 4(1H)-Quinolones by Thermolysis of Arylaminomethylene Meldrum's Acid Derivatives

References

• Cassis , R. , Tapia , R. and Valderrama , J. A. 1984 . J. Heterocyclic Chem. , 21 : 865
   Web of Science ®Google Scholar
• Cassis , R. , Tapia , R. and Valderrama , J. A. 1984 . ibid , 21 : 869
   Web of Science ®Google Scholar
• Cassis , R. and Valderrama , J. A. 1983 . Synth. Commun. , 13 : 347
   Web of Science ®Google Scholar
• Kaslow , C. E. and Young , V. V. 1950 . J. Am. Chem. Soc. , 72 : 5325 and references therein.
   Web of Science ®Google Scholar
• Reitsema , R. H. 1948 . Chem. Rev. , 43 : 43
   PubMed Web of Science ®Google Scholar
• Somanathan , R. and Smith , K. M. 1981 . J. Heterocyclic Chem. , 18 : 1077
   Web of Science ®Google Scholar
• Taylor , E. C. and Heindel , N. D. 1967 . J. Org. Chem. , 32 : 3339 and references therein.
   Web of Science ®Google Scholar
• Heindel , N. D. , Kennewell , P. D. and Fisch , V. B. 1969 . J. Heterocyclic Chem. , 6 : 77
   Web of Science ®Google Scholar
• British Patent . 1147760 . 1969 . (Chem. Abstr., 1969, 71, 49967a)
   Google Scholar
• Cassis , R. , Tapia , R. and Valderrama , J. A. in press . Synth. Commun. , For another application of Meldrum's acid in the synthesis of heterocycles see
   Google Scholar
• McNab , H. 1978 . Chem. Soc. Rev. , 7 : 345
   Web of Science ®Google Scholar
• Bihlmayer , G. A. , Derflinger , G. , Derkosch , J. and Polansky , O. E. 1967 . Monatsh. Chem. , 98 : 564
   Web of Science ®Google Scholar
• The products 4–10 were adequately characterized by IR11, NMR12 and by elemental analyses
   Google Scholar
• IR data (KBr), in cm−1: 4 3220 (NH), 1730, 1675 (C [dbnd] O), 1630(C [dbnd] C); 5 3180(NH), 1735, 1680(C [dbnd] O), 1620(C [dbnd] C); 6 3170(NH), 1718, 1680(C [dbnd] O), 1620(C [dbnd] C); 7 3170(NH), 1720, 1670(C [dbnd] O), 1625(C [dbnd] C); 8 3240 (NH), 1730, 1675(C [dbnd] O), 1625(C [dbnd] C); 9 3140(NH), 1730, 1690(C [dbnd] O), 1590(C [dbnd] C); 10 3240(NH), 1725, 1675(C [dbnd] O), 1630(C [dbnd] C).
   Google Scholar
• NMR data, in δ ppm, are as follows: 4 (C2D6CO) 1.72 (s, 6H, CH3), 7.60(m, 5H Ar), 8.70(d, 1H, J∼14Hz, CH), 11.2(br, s, 1H, NH); 5 (C2D6CO) 1.74(s, 6H, CH3), 2.39(s, 3H, CH3), 7.36(d, 2H, J∼9Hz, 2H Ar), 7.49(d, 2H, J∼9Hz, 2H Ar), 8.67(d, 1H, J∼14Hz, CH); 6 (C2D6CO) 1.72(s, 6H, CH3), 3.88(s, 3H, OCH3) 7.09(d, 2H, J∼9Hz, 2H Ar), 7.53(d, 2H, J∼9Hz, 2H Ar), 8.58(d, 1H, J∼14Hz, CH); 7 (C2D6SO/D2O) 1.70(s, 6H, CH3), 2.57(s, 3H, CH3CO), 7.71(d, 2H, J∼9Hz, 2H Ar), 8.03(d, 2H, J∼9 Hz, 2H Ar), 8.70(s, 1H, CH), 11.34 (s, 1H, NH); 8 (C2D6SO) 1.74(s, 6H, CH3), 7.87(d, 2H, J∼9Hz, 2h Ar), 8.31(d, 2H, J∼9Hz, 2H Ar), 8.73(d, 1H, J∼14Hz, CH), 11.44(d, 1H, J∼14Hz, NH); 9 (C2D6SO) 1.72(s, 6H, CH3), 7.46(dt, 1H, J∼2 and 8Hz, 1H Ar), 7.85(dt, 1H, J∼2 and 8Hz, 1H Ar), 8.08(br d, 1H, J∼8Hz, 1H Ar), 8.25(dd, 1H, J∼2 and 8Hz, 1H Ar), 8.77(d, 1H, J∼14Hz, CH), 12.68(br d, 1H, J∼14Hz, NH); 10(C2D6CO) 1.71(s, 6H, CH3), 3.87(s, 3H, OCH3), 3.97(s, 3H, OCH3), 6.84(dd, 1H, J∼3 and 9Hz, 1H Ar), 7.14(d, 1H, J∼9Hz, 1H Ar), 7.37(d, 1H, J∼3Hz, 1H Ar), 8.74(d, 1H, J∼14Hz, CH).
   Google Scholar
• Bouillon , G. and Schank , K. 1980 . Chem. Ber. , 113 : 2630
   Google Scholar
• The products 1, 11–16 were identified by their m. p. and NMR15 spectra.
   Google Scholar
• NMR data, in δ ppm are as follows: 11 (C2D6CO/D2O) 6.44(d, 1H, J∼7Hz), 7.4–7.6(m, 1H), 7.8(m, 2H), 8.14(d, 1H, J∼7Hz), 8.39(br d, 1H, J∼9Hz); 12 (C2D6CO) 2.47(s, 3H, CH3), 6.36(d, 1H, J∼7Hz), 7.60(s, 2H), 8.04(d, 1H, J∼7Hz), 8.11(br s, 1H); 13 (C2D6CO) 3.98(s, 3H, OCH3), 6.37(d, 1H, J∼7Hz), 7.37(dd, 1H, J∼3 and 9Hz), 7.69(d, 1H, J∼9Hz), 7.73(d, 1H, J∼3Hz); 14 (C2D6CO/D6O) 2.76(s, 3H, CH3CO), 6.42(d, 1H, J∼7Hz), 7.79(d, 1H, J∼9Hz), 8.12(d, 1H, J∼7Hz), 8.27(dd, 1H, J∼2 and 9 Hz), 8.95(d, 1H, J∼2Hz); 15 (C2-D6CO/CF3CO2H) 7.67(d, 1H, J∼6Hz), 8.46(d, 1H, J∼9Hz), 8.89(dd, 1H, J∼2 and 9Hz), 9.09(d, 1H, J∼6Hz), 9.49(d, 1H, J∼2Hz); 16 (C2D6SO) 6.22(d, 1H, J∼8Hz), 7.49(t, 1H, J∼8Hz), 7.96(br t, 1H, J∼8Hz), 8.54(dd, 1H, J∼2 and 8Hz), 8.62(dd, 1H, J∼2 and 8Hz), 11.8(br s, 1H, NH); 1 (D2O) 4.23(s, 3H, CH3O), 4.31(s, 3H, CH3O), 6.63(d, 1H, J∼7Hz), 7.06(d, 1H, J∼9Hz), 7.74(d, 1H, J∼9Hz), 8.24(d, 1H, J∼7Hz).
   Google Scholar
• Riegel , B. , Lappin , G. R. , Adelson , B. H. , Jackson , R. I. , Albisetti , C. J. Jr. , Dodson , R. M. and Baker , R. H. 1946 . J. Am. Chem. Soc. , 68 : 1264
   PubMed Web of Science ®Google Scholar
• Gordon , H. J. , Martin , J. C. and McNab , H. J. Chem. Soc., Chem. Commun. , 1983 957
   Google Scholar
• M. p. 153–154°C (Methanol). IR (KBr): 3240(NH), 1720, 1680(C [dbnd] O), 1600(C [dbnd] C)cm−1. NMR (C2D6CO): δ 1.74(s, 3H, CH3), 7.43(d, 1H, J∼4Hz), 7.61(d, 1H, J∼4Hz), 9.05(s, 1H, CH), 11.7(br s, 1H, NH) ppm.
   Google Scholar
• M. p. 175–176°C (methanol). IR (KBr): 3240 (NH), 1730, 1680 (C [dbnd] O), 1615 (C [dbnd] C) cm−1. NMR (C2D6SO): δ 1.75(s, 6H, CH3), 7.33(br t, 1H, J∼6Hz), 7.68(d, 1H, J∼8Hz), 7.95(br t, 1H J∼8Hz), 8.50(br d, 1H, J∼6Hz), 9.30(d, 1H, J∼14Hz, CH), 11.43(br d, 1H, J∼14Hz, NH) ppm.
   Google Scholar
• Dunwell , D. W. and Evans , D. J. Chem. Soc. (C) , 1971 2094
   Google Scholar
• Tamura , S. and Ono , M. 1978 . Chem. Pharm. Bull. , 26 : 3167
   Web of Science ®Google Scholar
• Lesher , G. Y. U. S. Patent . 3907798 . 1975 . (Chem. Abstr., 1976, 84, 44130f) Sterling Drug, Inc.
   Google Scholar
• While we were preparing this manuscript, Cimino et al23, in a recent paper have reported the synthesis of compound 1 using Heindel's method5 to elucidate the structure of 3, 5, 8-trihydroxy-4 (1H)-quinolone found in the sponge Verongia aerophoba Schmidt.
   Google Scholar
• Cimino , G. , De Rosa , S. , De Stefano , S. , Spinella , A. and Sodano , G. 1984 . Tetrahedron Lett. , 25 : 2925
   Web of Science ®Google Scholar