New conditions for synthesis of (plusmn;)-2-monosubstituted and (plusmn;)-2,2-disubstituted 2,3-dihydro-4(1H)-quinazolinones from 2-nitro- and 2-aminobenzamide

Journal of Heterocyclic Chemistry

Volumn 48, Issue 5, 2011, Pages 991-997

  Bunce, Richard A ^a   Nammalwar, Baskar ^a  

^a OKLAHOMA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 CHLOROPHENYL) 2,3 DIHYDRO 4 (1H) QUINAZOLINONE; 2 (2 CHLOROPHENYL) 2,3 DIHYDRO 4(1H) QUINAZOLINONE; 2 AMINOBENZAMIDE; 2 BENZYL 2,3 DIHYDRO 2 METHYL 4(1H) QUINAZOLINONE; 2 BUTYL 2,3 DIHYDRO 4(1H) QUINAZOLINONE; 2,3 DIHYDRO 2 (2 PHENYLETHENYL) 4(1H) QUINAZOLINONE; 2,3 DIHYDRO 2 (4 METHOXYPHENYL) 4 (1H) QUINAZOLINONE; 2,3 DIHYDRO 2 (4 METHOXYPHENYL) 4(1H) QUINAZOLINONE; 2,3 DIHYDRO 2 [4 (TRIFLUOROMETHYL)PHENYL] 4(1H) QUINAZOLINONE; 2,3 DIHYDRO 2 METHYL 2 (PHENYLMETHYL) 4 (1H) QUINAZOLINONE; 2,3 DIHYDRO 2 METHYL 2 PHENYL 4(1H) QUINAZOLINONE; 2,3 DIHYDRO 2 METHYL 2 PROPYL 4 (1H) QUINAZOLINONE; 2,3 DIHYDRO 2 PHENYL 4(1H) QUINAZOLINONE; 2,3 DIHYDRO 2,2 DIMETHYL 4 (1H) QUINAZOLINONE; 2,3 DIHYDRO 2,2 DIPHENYL 4 (1H) QUINAZOLINONE; 2,4 (1H,3H) QUINAZOLINEDIONE; 6,6A DIHYDROISOINDOLO(2,1 A)QUINAZOLINE 5,11 DIONE; ACETIC ACID; ALDEHYDE; BENZAMIDE DERIVATIVE; ETHYL 4 (1,2,3,4 TETRAHYDRO 4 OXOQUINAZOLIN 2 YL)BUTANOATE; ETHYL 5 (1,2,3,4 TETRAHYDRO 4 OXOQUINAZOLIN 2 YL)PENTANOATE; KETONE; METHYL 3 (1,2,3,4 TETRAHYDRO 2 METHYL 4 OXOQUINAZOLIN 2 YL)PROPANOATE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 80053217746     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.672     Document Type: Article

References (40)

1. (a), Wolfe, J. F.; Rathman, T. L.; Sleevi, M. C.; Campbell, J. A.; Greenwood, T. D., J Med Chem 1990, 33, 161
2. (b), Padia, J. K.; Field, M.; Hinton, J.; Meecham, K.; Pablo, J.; Pinnock, R.; Roth, B. D.; Singh, L.; Suman-Chauhan, N.; Trivedi, B. K.; Webdale, L., J Med Chem 1998, 41, 1042.
3. (a), Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.; Nakanishi, Y.; Hamel, E.; Lee, K.-H., J Med Chem 2000, 43, 4479
4. (b), Chinigo, G. M.; Paige, M.; Grindrod, S.; Hamel, E.; Dakshanamurthy, S.; Chruszcz, M.; Minor, W.; Brown, M. L., J Med Chem 2008, 51, 4620.
5. Ozaki, K.; Yamada, Y.; Oine, T.; Ishizuka, T.; Iwasawa, Y., J Med Chem 1985, 28, 568.
6. Gouliaev, A. H.; Larsen, M.; Varming, T.; Mathiesen, C.; Johansen, T. H.; Scheel,-Kruger, J.; Olsen, G. M.; Nielsen, E. O., World Pat. WO 9942456, 1999; Chem Abstr 1999, 131, 184974.
7. (a), Yale, H. L.; Kalkstein, M., J Med Chem 1967, 10, 334
8. (b), Alaimo, R. J.; Russell, H. E., J Med Chem 1972, 15, 335
9. (c), Wen, H.; Hao, W.; Gong, B., Zhongguo Kangshengsu Zazhi 2002, 27, 644; Chem Abstr 2004, 140, 399618.
10. Gupta, R. C.; Nath, R.; Shanker, K.; Bhargava, K. P.; Kishor, K., J Ind Chem Soc 1979, 56, 219.
11. (a), Orme, M. W.; Baindur, N.; Robbins, K. G.; Harris, S. M.; Kontoyianni, M.; Hurley, L. H.; Kerwin, S. M.; Mundy, G. R.; Robbins, K. G.,; Petrie, C. Int. Pat. WO 9817267, 1998; Chem Abstr 1998, 128, 321662
12. (b), Petrie, C.; Orme, M. W.; Baindur, N.; Robbins, K. G.; Harris, S. M.; Kontoyianni, M.; Hurley, L. H.; Kerwin, S. M.; Mundy, G. R., Int. Pat. WO 9715308, 1998; Chem Abstr 1997, 127, 17703.
13. (a), Biressi, M. G.; Cantrelli, G.; Carissimi, M.; Cattaneo, A.; Ravenna, F., Farmaco Ed Sci 1969, 24, 199; Chem Abstr 1969, 71, 61357
14. (b), Parish, H. A., Jr.; Gilliom, R. D.; Purcell, W. P.; Browne, R. K.; Spirk, R. F.; White, H. D., J Med Chem 1982, 25, 98.
15. Bhalla, P. R.; Walworth, B. L., U.S. Pat. 4,431,440, 1984; Chem Abstr 1984, 100, 174857.
16. Bunce, R. A.; Randall, M. H.; Applegate, K. G., Org Prep Proced Int 2002, 34, 493.
17. Bunce, R. A.; Schammerhorn, J. E., J Heterocycl Chem 2006, 43, 1031.
18. Bunce, R. A.; Nammalwar, B., J Heterocycl Chem 2009, 46, 172.
19. Bunce, R. A.; Nammalwar, B., J Heterocycl Chem 2009, 46, 854.
20. Shi, D.-Q.; Rong, L.-C.; Wang, J.-X.; Wang, X.-S.; Tu., S.-J.; Hu, H.-W., Gaodeng Xuexiao Huaxue Xuebao 2004, 25, 2051; Chem Abstr 2005, 153, 266896.
21. Su, W.; Yang, B., Aust J Chem 2002, 55, 695.
22. Cai, G.; Xu, X.; Li, Z.; Weber, W. P.; Lu, P., J Heterocycl Chem 2002, 39, 1271.
23. Chen, J.; Wu, D.; He, F.; Liu, M.; Wu, H.; Ding, J.; Su, W., Tetrahedron Lett 2008, 49, 3814.
24. Chen, J. X.; Wu, H. Y.; Su, W. K., Chin Chem Lett 2007, 18, 536; Chem Abstr 2008, 148, 517663.
25. Qiao, R. Z.; Xu, B. L.; Wang, Y. H., Chin Chem Lett 2007, 18, 656; Chem Abstr 2008, 148, 517638.
26. Salehi, P.; Dabiri, M.; Baghbanzadeh, M.; Bahramnejad, M., Synth Commun 2006, 36, 2287.
27. Baghbanzedeh, M.; Salehi, P.; Dabiri, M.; Kozehgary, G., Synthesis 2006, 344.
28. Surpur, M. P.; Singh, P. R.; Patil, S. B.; Samant, S. D., Synth Commun 2007, 37, 1965.
29. Shaterian, H. R.; Oveisi, A. R.; Honarmand, M., Synth Commun 2010, 40, 1231.
30. Shaabani, A.; Maleki, A.; Mofakham, H., Synth Commun 2008, 38, 3751.
31. Although this paper was in review, a report detailing the synthesis of 6 and related compounds using a similar strategy appeared, see, Wang, M.; Dou, G.; Shi, D., J Comb Chem 2010, 12, 582.
32. Bordwell, F. G., Acc Chem Res 1988, 21, 456; The larger pKa of the aniline protons (30.6) vs benzamide (23.4) protons indicates that the aniline nitrogen is more basic and, therefore, more nucleophilic.
33. It was well known that these conditions do not hydrogenolyze aromatic halides, see, Mosley, W. L., J Org Chem 1959, 24, 421 and ref 10, but less was known about aliphatic halides such as 9.
34. Aeberli, P.; Houlihan, W., J Org Chem 1968, 33, 2402.
35. Osuka, A.; Nakajima, S.; Maruyama, K., J Org Chem 1992, 57, 7355.
36. Still, W. C.; Kahn, M.; Mitra, A., J Org Chem 1978, 43, 2923.
37. Xu, G.; Micklatcher, M.; Silvestri, M. A.; Hartman, T. L.; Burrier, J.; Osterling, M. C.; Wargo, H.; Turpin, J. A.; Buckheit R. W., Jr.; Cushman, M., J Med Chem 2001, 44, 4092.
38. Wilson, J. E.; Casarez, A. D.; MacMillan, D. W. C., J Am Chem Soc 2009, 131, 11332.
39. Larsen, S. D.; Connell, M. A.; Cudahy, M. M.; Evans, B. R.; May, P. D.; Meglasson, M. D.; O'Sullivan, T. J.; Schostarez, H. J.; Sih, J. C.; Stevens, F. C.; Tanis, S. P.; Tegley, C. M.; Tucker, J. A.; Vaillancourt, V. A.; Vidmar, T. J.; Watt, W.; Yu, J. H., J Med Chem 2001 44, 1217.
40. Jiarong, L.; Xian, C.; Daxin, S.; Shuling, M.; Qing, L.; Qi, Z.; Jianhong, T., Org Lett 2009, 11, 1193.