메뉴 건너뛰기




Volumn , Issue 11, 2009, Pages 1847-1851

Regioselective synthesis of quinolin-4-ones by pyrolysis of anilinomethylene derivatives of Meldrum's acid

Author keywords

Flash vacuum pyrolysis; Meldrum's acid; Quinolin 4 ones

Indexed keywords

ANILINOMETHYLENE DERIVATIVE; CARBENE; IMIDOYLKETENE; KETENE DERIVATIVE; QUINOLIN 4 ONE DERIVATIVE; QUINOLINE; UNCLASSIFIED DRUG;

EID: 67650080769     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217383     Document Type: Article
Times cited : (8)

References (26)
  • 1
    • 67650037089 scopus 로고    scopus 로고
    • Sterling Drug Inc. Brit.; 1,147,760 Chem. Abstr. 1969, 71, 49967a.
    • (a) Sterling Drug Inc. Brit.; 1,147,760 Chem. Abstr. 1969, 71, 49967a.
  • 12
    • 67650025510 scopus 로고    scopus 로고
    • Prior isolation of 1 provides much cleaner products 2 (≥? 95% yield) than the one-pot method reported in ref. 5.
    • Prior isolation of 1 provides much cleaner products 2 (≥? 95% yield) than the one-pot method reported in ref. 5.
  • 14
    • 67650030888 scopus 로고    scopus 로고
    • 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
    • 3J = 7.6 Hz), 4.30 (3 H, s), see Figure 3.
  • 17
    • 67650013877 scopus 로고    scopus 로고
    • 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,
    • 3J = 7.2 Hz).
  • 22
    • 67650028542 scopus 로고    scopus 로고
    • 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).
  • 24
    • 67650062791 scopus 로고    scopus 로고
    • 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
    • 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.
  • 25
    • 67650059673 scopus 로고    scopus 로고
    • 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
    • 3J = 6.9 Hz).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.