Reaction of imidoformates with anthranilates: Facile, one-pot, three-component synthesis of 8H-quinazolino[4,3-b]quinazolin-8-ones

Journal of Heterocyclic Chemistry

Volumn 50, Issue 5, 2013, Pages 1089-1093

  Venkateswarlu, S ^a   Satyanarayana, M ^a   Ravikiran, P ^a   Siddaiah, V ^b  

^a Laila Impex Research Centre   (India)

^b ANDHRA UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

10 BROMO 2,3 DIMETHOXY 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; 10 CHLORO 2,3 DIMETHOXY 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; 10 METHYL 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; 2 AMINOBENZONITRILE; 2,3 DIMETHOXY 10 METHYL 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; 2,3 DIMETHOXY 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; 3 CHLORO 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; 8H QUINAZOLINO[4,3 B]QUINAZOLIN 8 ONE; ACETIC ACID; AMIDE; ANTHRANILIC ACID DERIVATIVE; BENZENE DERIVATIVE; ESTER; FORMIC ACID; QUINAZOLINONE DERIVATIVE; TRIETHYL ORTHOFORMATE; UNCLASSIFIED DRUG;

ARTICLE; METHODOLOGY; ONE POT SYNTHESIS; ORGANIC CHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 84884905612     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.1603     Document Type: Article

References (41)

1. (a), Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Comprehensive Heterocyclic Chemistry II; Pergamon: Oxford, 1996
2. (b), Joule, J. A.; Mills, K., Heterocyclic Chemistry; Blackwell Science: Oxford, 2000.
3. (a), Nicolaou, K. C.; Vourloumis, D.; Winssinger, N.; Baran, P. S., Angew Chem Int Ed 2000, 39, 44
4. (b), Arya, P.; Chou, D. T. H.; Baek, M.-G., Angew Chem Int Ed 2001, 40, 339.
5. (a), Michael, J. P., Nat Prod Rep 2001, 18, 543
6. (b), Reddy, P. S.; Reddy, P. P.; Vasantha, T., Heterocycles 2003, 60, 183
7. (c), Horton, D. A.; Bourne, G. T.; Smythe, M. L., Chem Rev 2003, 103, 893.
8. (a), Hennequin, L. F.; Thomas, A. P.; Johnstone, C.; Stokes, E. S. E.; Ple, P. A.; Lohmann, J.-J. M.; Ogilvie, D. J.; Dukes, M.; Wedge, S. R.; Curwen, J. O.; Kendrew, J.; Brempt, C. L., J Med Chem 1999, 42, 5369
9. (b), Seijas, J. A.; Vazquez-Tato, M. P.; Martinez, M. M., Tetrahedron Lett 2000, 41, 2215
10. (c), Rewcastle, G. W.; Denny, W. A.; Bridges, A. J.; Zhou, H.; Cody, D. R.; McMichael, A.; Fry, D. W., J Med Chem 1995, 38, 3482
11. (d), Wang, J.-Q.; Gao, M.; Miller, K. D.; Sledge, G. W.; Zheng, Q.-H., Bioorg Med Chem Lett 2006, 16, 4102.
12. Stephen, T.; Stephen, H., J Chem Soc 1956, 4173.
13. Butler, K.; Partridge, M. W.; Waite, J. A., J Chem Soc 1960, 4970.
14. Alexandre, F.-R.; Berecibar, A.; Wrigglesworth, R.; Besson, T., Tetrahedron 2003, 59, 1413.
15. Hu, Z.; Li, S.-d.; Hong, P.-z., Arkivoc 2010, 9, 171.
16. (a), Shestopalov, A. M.; Shestopalov, A. A.; Rodinovskaya, L. A., Synthesis 2008, 1
17. (b), Domling, A.; Ugi, I., Angew Chem Int Ed 2000, 39, 3168
18. (c), Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P., Chem Eur J 2000, 6, 3321
19. (d), Orru, R. V. A.; de Greef, M., Synthesis 2003, 1471
20. (e), Weber, L.; Illgen, K.; Almstetter, M., Synlett 1999, 366
21. (f), Kobayashi, S., Chem Soc Rev 1999, 28, 1.
22. (a), Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J., Tetrahedron 2005, 61, 10153
23. (b), Mhaske, S. B.; Argade, N. P., J Org Chem 2004, 69, 4563
24. (c), Kamal, A.; Reddy, K. S.; Prasad, B. R.; Babu, A. H.; Ramana, A. V., Tetrahedron Lett 2004, 45, 6517
25. (d), Takeuchi, H.; Hagiwara, S.; Eguchi, S., Tetrahedron 1989, 45, 6375
26. (e), Li, F.; Feng, Y.; Meng, Q.; Li, W.; Li, Z.; Wang, Q., Arkivoc 2007, 1, 40
27. (f), Gupton, J. T.; Correia, K. F.; Hertel, G. R., Synth Commun 1984, 14, 1013.
28. (a), Marinho, E.; Araujo, R.; Proenca, F., Tetrahedron 2010, 66, 8681
29. (b), Kobayashi, K.; Ukon, T.; Nakano, H.; Fukamachi, S.; Konishi, H., Synthesis 2008, 2874
30. (c), Campbell, S. F.; Hardstone, J. D.; Palmer, M. J., Tetrahedron Lett 1984, 25, 4813
31. (d), Gupton, J. T.; Miller, J. F.; Bryant, R. D.; Maloney, P. R.; Foster, B. S., Tetrahedron 1987, 43, 1747
32. (e), Leiby, R. W., J Org Chem 1985, 50, 2926
33. (f), Brown, D. J.; Lenaga, K., J Chem Soc Perkin Trans 1 1975, 2182
34. (g), Taylor, E. C.; Mckillop, A.; Shvo, Y.; Hawks, G. H., Tetrahedron 1967, 23, 2081.
35. (a), Foucourt, A.; Dubouilh-Benard, C.; Chosson, E.; Corbiere, C.; Buquet, C.; Iannelli, M.; Leblond, B.; Marsais, F.; Besson, T., Tetrahedron 2010, 66, 4495
36. (b), Fischer, R. W.; Misun, M., Org Proc Res Dev 2001, 5, 581
37. (c), Chandregowda, V.; Rao, G. V.; Reddy, G. C., Org Proc Res Dev 2007, 11, 813
38. (d), Yoon, D. S.; Han, Y.; Stark, T. M.; Haber, J. C.; Gregg, B. T.; Stankovich, S. B., Org Lett 2004, 6, 4775
39. (e), Domarkas, J.; Dudouit, F.; Williams, C.; Qiyu, Q.; Banerjee, R.; Brahimi, F.; Jean-Claude, B. J., J Med Chem 2006, 49, 3544
40. (f), Albuschat, R.; Lowe, W.; Weber, M.; Luger, P.; Jendrossek, V., Eur J Med Chem 2004, 39, 1001
41. (g), Tsou, H.-R.; Mamuya, N.; Johnson, B. D.; Reich, M. F.; Gruber, B. C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, F. E.; Greenberger, L. M.; Wang, Y.-F.; Wissner, A., J Med Chem 2001, 44, 2719.