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1
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67650037089
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Sterling Drug Inc. Brit.; 1,147,760 Chem. Abstr. 1969, 71, 49967a.
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(a) Sterling Drug Inc. Brit.; 1,147,760 Chem. Abstr. 1969, 71, 49967a.
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2
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84943961938
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(b) Cassis, R.; Tapia, R.; Valderrama, J. A. Synth. Commun. 1985, 15, 125.
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(1985)
Synth. Commun
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Cassis, R.1
Tapia, R.2
Valderrama, J.A.3
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3
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63849329381
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(c) Rotzoll, S.; Reinke, H.; Fischer, C.; Langer, P. Synthesis 2009, 69.
-
(2009)
Synthesis
, pp. 69
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Rotzoll, S.1
Reinke, H.2
Fischer, C.3
Langer, P.4
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4
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37049099617
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Gordon, H. J.; Martin, J. C.; McNab, H. J. Chem. Soc., Chem. Commun. 1983, 957.
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(1983)
J. Chem. Soc., Chem. Commun
, pp. 957
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Gordon, H.J.1
Martin, J.C.2
McNab, H.3
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5
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0001675020
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Briehl, H.; Lukosch, A.; Wentrup, C. J. Org. Chem. 1984, 49, 2772.
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(1984)
J. Org. Chem
, vol.49
, pp. 2772
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Briehl, H.1
Lukosch, A.2
Wentrup, C.3
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7
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34548735922
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Al-Awadi, N. A.; Abdelhamid, I. A.; Al-Etaibi, A. M.; Elnagdi, M. H. Synlett 2007, 2205.
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(2007)
Synlett
, pp. 2205
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Al-Awadi, N.A.1
Abdelhamid, I.A.2
Al-Etaibi, A.M.3
Elnagdi, M.H.4
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10
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33645666865
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George, L.; Netsch, K.-P.; Penn, G.; Kollenz, G.; Wentrup, C. Org. Biomol. Chem. 2006, 4, 558.
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(2006)
Org. Biomol. Chem
, vol.4
, pp. 558
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George, L.1
Netsch, K.-P.2
Penn, G.3
Kollenz, G.4
Wentrup, C.5
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12
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67650025510
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-
Prior isolation of 1 provides much cleaner products 2 (≥? 95% yield) than the one-pot method reported in ref. 5.
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Prior isolation of 1 provides much cleaner products 2 (≥? 95% yield) than the one-pot method reported in ref. 5.
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13
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33748421870
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Hirano, J.; Hamase, K.; Zaitsu, K. Tetrahedron 2006, 62, 10065.
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(2006)
Tetrahedron
, vol.62
, pp. 10065
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Hirano, J.1
Hamase, K.2
Zaitsu, K.3
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14
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67650030888
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FVP of 2b (0.600 g, Tf, 600°C, T i, 170°C, t, 50 min, P, 2.3.10-5 bar) gave a yellow solid (0.403 g, quant, recrystallization from MeOH gave 6-methoxy-1H-quinolin-4-one (3b, 0.234 g, 61, mp 243-246°C (from MeOH; lit.11 251-252°C, 1H NMR (360 MHz, DMSO-d6, δ, 11.78 (1 H, br s, 7.87 (1 H, d, 3J, 7.2 Hz, 7.53-7.52 (2 H, m, 7.30 (1 H, dd, 3J, 9.1 Hz, 4J, 2.1 Hz, 6.03 (1 H, d, 3J, 7.2 Hz, 3.85 (3 H, s, see Figure 1. FVP of 2c (0.704 g, Tf, 600°C, Ti, 160°C, t, 1 h, P, 1.9·10-5 bar) gave a yellow solid (0.414 g, 93, in which the ratio 3ca/3cb was 7:93 by 1H NMR spectroscopy, and which provided pure 7-methoxy-1H-quinolin-4-one 3cb, 0.277 g
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3J = 7.6 Hz), 4.30 (3 H, s), see Figure 3.
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-
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15
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84872622570
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Lauer, W. M.; Arnold, R. T.; Tiffany, B.; Tinker, J. J. Am. Chem. Soc. 1946, 68, 1268.
-
(1946)
J. Am. Chem. Soc
, vol.68
, pp. 1268
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Lauer, W.M.1
Arnold, R.T.2
Tiffany, B.3
Tinker, J.4
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16
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33947378884
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-
For example, see
-
For example, see: Harrison, A. G.; Honnen, L. R.; Dauben, H. J. Jr.; Lossing, F. P. J. Am. Chem. Soc. 1960, 82, 5593.
-
(1960)
J. Am. Chem. Soc
, vol.82
, pp. 5593
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Harrison, A.G.1
Honnen, L.R.2
Dauben Jr., H.J.3
Lossing, F.P.4
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17
-
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67650013877
-
-
FVP of 2e (0.610 g, Tf, 600°C, T i, 200°C, t, 1.25 h, P, 3.1.10-5 bar) gave 6-cyano-1H-quinolin-4-one16 (3e) as an orange solid (0.358 g, 94, mp 186°C (from MeOH, 1H NMR (250 MHz, DMSO-d6, δ, 8.47 (1 H, dd, 4J, 1.9 Hz, 5J, 0.5 Hz, 8.06 (1 H, d, 3J, 7.6 Hz, 8.02 (1 H, dd, 3J, 8.7 Hz, 4J, 1.9 Hz, 7.72 (1 H, dd, 3J, 8.7 Hz, 5J, 0.5 Hz, 6.20 (1 H, d, 3J, 7.6 Hz, FVP of 2f (0.306 g, Tf, 650°C, Ti, 210°C, t, 25 min, P, 4.0.10-5 bar) gave a ca. 25:75 mixture of 5- and 7-cyano-1H-quinolin-4-ones17 (3fa and 3fb; 0.176 g, 94, 1H NMR 250 MHz, DMSO-d6,
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3J = 7.2 Hz).
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-
-
-
18
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33947247616
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Reported by
-
Reported by: Margolis, B. J.; Long, K. A.; Laird, D. L. T.; Ruble, J. C.; Pulley, S. R. J. Org. Chem. 2007, 72, 2232.
-
(2007)
J. Org. Chem
, vol.72
, pp. 2232
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-
Margolis, B.J.1
Long, K.A.2
Laird, D.L.T.3
Ruble, J.C.4
Pulley, S.R.5
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19
-
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33947442535
-
-
Reported by
-
Reported by: Price, C. C.; Snyder, H. R.; Bullitt, O. H. Jr.; Kovacic, P. J. Am. Chem. Soc. 1947, 69, 374.
-
(1947)
J. Am. Chem. Soc
, vol.69
, pp. 374
-
-
Price, C.C.1
Snyder, H.R.2
Bullitt Jr., O.H.3
Kovacic, P.4
-
20
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0025639162
-
-
Sashida, H.; Kaname, M.; Tsuchiya, T. Chem. Pharm. Bull. 1990, 38, 2919.
-
(1990)
Chem. Pharm. Bull
, vol.38
, pp. 2919
-
-
Sashida, H.1
Kaname, M.2
Tsuchiya, T.3
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21
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33947298558
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-
For example, see
-
For example, see: Fields, E. K.; Meyerson, S. Acc. Chem. Res. 1969, 2, 273.
-
(1969)
Acc. Chem. Res
, vol.2
, pp. 273
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-
Fields, E.K.1
Meyerson, S.2
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22
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67650028542
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-
FVP of 2h (0.664 g, Tf, 600°C, T i, 200°C, t, 1 h, P, 3.2.10-5 bar) gave 6-nitro-1H-quinolin-4-one (3h, 0.283 g, 66, mp >320°C (from MeOH; lit.21 337-342°C, 1H NMR (250 MHz, DMSO-d6, δ, 8.88 (1 H, d, 3J, 2.8 Hz, 8.46 (1 H, dd, 3J, 9.2 Hz, 4J, 2.8 Hz, 8.09 (1 H, d, 3J, 7.9 Hz, 7.76 (1 H, dd, 3J, 9.2 Hz, 5J, 0.5 Hz, 6.24 1 H, d, 3J, 7.9 Hz
-
3J = 7.9 Hz).
-
-
-
-
23
-
-
0002702291
-
-
Heindel, N. D.; Kennewell, P. D.; Fish, V. B. J. Heterocycl. Chem. 1969, 6, 77.
-
(1969)
J. Heterocycl. Chem
, vol.6
, pp. 77
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-
Heindel, N.D.1
Kennewell, P.D.2
Fish, V.B.3
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24
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67650062791
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Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A. Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith
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Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A. Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03; Gaussian, Inc.: Wallingford CT, 2004.
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25
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67650059673
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FVP of 7 (0.323 g, Tf, 600°C, T i, 200°C, t, 1 h, P, 3.3.10-5 bar) gave a yellow solid (0.182 g) and recrystallization from MeOH provided 1H-benzo[4,5]imidazo[1,2-a]pyrimidin-4-one (8, 0.129 g, 62, mp 285-287°C (from MeOH; lit.24 290°C, 1H NMR (250 MHz, DMSO-d6, δ, 8.45 (1 H, d, 3J, 8.0 Hz, 8.00 (1 H, d, 3J, 6.9 Hz, 7.58 (1 H, d, 3J, 7.6 Hz, 7.50 (1 H, td, 3J, 7.6 Hz, 4J, 1.3 Hz, 7.34 (1 H, td, 3J, 8.0 Hz, 4J, 1.3 Hz, 5.99 1 H, d, 3J, 6.9 Hz
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3J = 6.9 Hz).
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