2466
T. Boisse et al. / Tetrahedron 65 (2009) 2455–2466
cmꢁ1:1278,1340,
W. D. J. Org. Chem. 1994, 59, 2623; (c) Bowman, W. R.; Bridge, C. F.; Cloonan, M.
147.5(C),149.3(C),154.0(C),160.4(C),169.6(C);IRn
O.; Leach, D. C. Synlett 2001, 765; (d) Govindachari, T. R.; Ravindranath, K. R.;
Viswanathan, N. J. Chem. Soc., Perkin Trans. 1 1974, 1215.
1518,1578,1668,1749. Anal. Calcd for C20H15N3O5: C, 63.66;H, 4.01;N,
11.14. Found: C, 63.30; H, 4.32; N, 11.15.
11. (a) Pendrak, I.; Wittrock, R.; Kingsbury, W. D. J. Org. Chem. 1995, 60, 2912; (b)
Zhang, W.; Luo, Z.; Chen, C. H.-T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443.
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J. Med. Chem. 1994, 37, 3434.
4.18.4. Methyl 3-{[4-(acetyloxy)-3,5-dimethoxyphenyl]hydrazono}-
9-oxo-1,2,3,9-tetrahydropyrrolo[2,1-b]quinazoline-1-
carboxylate (70)
White powder; 87% yield; mp (acetonitrile) 257–259 ꢀC; TLC Rf
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(EtOAc/heptane 70/30)¼0.6; 1H NMR (CDCl3, 200 MHz)
d ppm: 2.37
(s, 3H, OCOCH3), 3.29 (ddd, J¼17.5, 3.7, 2.5 Hz, 1H, CHCH2C]CH),
3.65 (ddd, J¼17.5, 10.2, 2.5 Hz, 1H, CHCH2C]CH), 3.82 (s, 3H,
CO2CH3), 3.88 (s, 6H, 2ꢂOCH3), 5.26 (dd, J¼10.2, 3.7 Hz, 1H,
CHCH2C]CH), 6.77 (s, 2H, ArH), 7.47 (ddd, J¼8.4, 5.1, 3.5 Hz, 1H,
ArH), 7.75–7.80 (m, 2H, ArH), 7.83 (t, J¼2.5 Hz, 1H, CHCH2C]CH),
´
14. (a) Bencteux, E.; Houssin, R.; Henichart, J.-P. J. Heterocycl. Chem.1997, 34,1375; (b)
Bouey-Bencteux, E.; Loison, C.; Pommery, N.; Houssin, R.; He´nichart, J.-P. Anti-
Cancer Drug Des. 1998, 13, 893; (c) Catrycke, M.-O.; Houssin, R.; He´nichart, J.-P.;
Pfeiffer, B.; Renard, P.; Dassonneville, L.; Bailly, C. Bioorg. Med. Chem. Lett. 1999, 9,
2025; (d) Goossens, J.-F.; Bouey-Bencteux, E.; Houssin, R.; He´nichart, J.-P.; Colson,
P.; Houssier, C.; Laine, W.; Baldeyrou, B.; Bailly, C. Biochemistry 2001, 40, 4663; (e)
Dudouit, F.; Houssin, R.; He´nichart, J.-P. J. Heterocycl. Chem. 2001, 38, 755.
15. Malecki, N.; Houssin, R.; He´nichart, J.-P.; Couturier, D.; Petra, F.; Legentil, L.;
Rigo, B. J. Heterocycl. Chem. 2005, 40, 45.
8.30 (d, J¼7.7 Hz, 1H, ArH); 13C NMR (CDCl3, 50 MHz)
d ppm: 20.5
(CH3), 30.6 (CH2), 53.1 (CH3), 56.3 (2ꢂCH3), 56.9 (CH),106.7 (2ꢂCH),
121.0 (C), 126.6 (CH), 126.8 (CH), 127.5 (CH), 129.2 (C), 131.5 (CH),
133.4 (C), 134.7 (CH), 149.7 (C), 152.5 (3ꢂC), 154.8 (C), 160.7 (C),
168.6 (C), 169.9 (C); IR
n
cmꢁ1: 1122, 1185, 1210, 1587, 1676, 1746,
16. Brunin, T.; He´nichart, J.-P.; Rigo, B. Tetrahedron 2005, 61, 7916.
´
17. Brunin, T.; Legentil, L.; Henichart, J.-P.; Rigo, B. Tetrahedron 2006, 62, 3959.
1757. Anal. Calcd for C24H22N2O7: C, 64.00; H, 4.92; N, 6.22. Found:
C, 64.34; H, 5.21; N, 6.44.
18. (a) Friedla¨nder, P. Chem. Ber. 1882, 15, 2572; (b) Cheng, C. C.; Yan, S. J. Org. React.
1982, 28, 37; (c) Wu, J.; Zhang, L.; Diao, T.-N. Synlett 2005, 2653; (d) De, S. K.;
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19. (a) Cauliez, P.; Rigo, B.; Fasseur, D.; Couturier, D. J. Heterocycl. Chem. 1991, 28,
1143; (b) Fasseur, D.; Rigo, B.; Leduc, C.; Cauliez, P.; Couturier, D. J. Heterocycl.
Chem. 1992, 29, 1285.
Acknowledgements
The authors would like to thank the Region Nord-Pas-de-Calais
for T.B.’s scholarship.
20. Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2001, 66, 9038.
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