Efficient synthesis of mono- and disubstituted 2,3-dihydroquinazolin-4(1H)-ones
839
9. Khurana JM, Kukreja G (2003) J Heterocycl Chem 40:677
10. Yoo CL, Fettinger JC, Kurth MJ (2005) J Org Chem 70:6941
11. Rao VB, Ratnam CV (1979) Indian J Chem Sect B 18B:409
12. Moore JA, Sutherland GJ, Sowerby R, Kelly EG, Palermo S,
Webster W (1969) J Org Chem 34:887
13. Yale HL (1977) J Heterocycl Chem 14:1357
14. Salehi P, Dabiri M, Zolfigol MA, Baghbanzadeh M (2005)
Synlett 1155
6.9 Hz, 1H), 7.53 (t, J = 6.9 Hz, 1H), 7.35 (t, J = 7.4 Hz,
1H), 7.27 (d, J = 7.8 Hz, 1H), 2.80 (d, J = 4.6 Hz, 3H)
ppm; 13C NMR (125 MHz, DMSO-d6): d = 160.2, 149.0,
148.3, 141.1, 131.2, 129.9, 129.7, 129.2, 126.5, 124.0,
119.0, 70.1, 26.1 ppm; LC/MS: m/z (%) = 284 ([M ?
H]?, 100), 282 (22).
15. Dabiri M, Salehi P, Otokesh S, Baghbanzadeh M, Kozehgary G,
Mohammadi AA (2005) Tetrahedron Lett 46:6123
16. Baghbanzadeh M, Salehi P, Dabiri M, Kozehgary G (2006)
Synthesis 344
17. Dabiri M, Salehi P, Baghbanzadeh M, Zolfigol MA, Agheb M,
Heydari S (2008) Catal Commun 9:785
18. Wang LM, Hu L, Shao JH, Yu JJ, Zhang L (2008) J Fluorine
Chem 129:1139
19. Chen JX, Wu DZ, He F, Liu M, Wu HY, Ding JC, Su WK (2008)
Tetrahedron Lett 49:3814
20. Chen JX, Su WK, Wu HY, Liu MC, Jin C (2007) Green Chem
9:972
21. Darvatkar NB, Bhilare SV, Deorukhkar AR, Raut DG, Salunkhe
MM (2010) Green Chem Lett Rev 3:301
22. Shaterian HR, Oveisi AR, Honarmand M (2010) Synth Commun
40:1231
23. Dabiri M, Salehi P, Bahramnejad M, Alizadeh M (2010) Monatsh
Chem 141:877
2,3-Dihydro-2-phenyl-3-propylquinazolin-4(1H)-one
(3u, C17H18N2O)
White crystals; m.p.: 126–127 °C; IR (KBr): v = 3,303,
3,065, 2,360, 1,630, 1,588, 1,507, 1,458, 748 cm-1; H
1
NMR (500 MHz, DMSO-d6): d = 7.65 (dd, J = 1.2,
6.5 Hz, 1H), 7.34-7.27 (m, 6H), 7.18 (dt, J = 1.5,
6.8 Hz, 1H), 6.66–6.62 (m, 2H), 5.83 (d, J = 2.5 Hz,
1H), 3.86–3.81 (m, 1H), 2.75–2.69 (m, 1H), 1.63–1.41 (m,
2H), 0.82 (t, J = 7.4 Hz, 3H) ppm; 13C NMR (125 MHz,
DMSO-d6): d = 162.2, 146.2, 141.2, 133.0, 128.4, 128.2,
127.3, 126.0, 117.0, 115.0, 114.2, 70.1, 46.0, 20.7,
11.1 ppm; LC/MS: m/z (%) = 267 ([M ? H]?, 100), 268
(19).
Acknowledgments We are grateful to the Committee of Science
and Technology of Liaoning Province of China for financial support
(No. 20091001).
24. Salehi P, Dabiri M, Baghbanzadeh M, Bahramnejad M (2006)
Synth Commun 36:2287
25. Surpur MP, Singh PR, Patil SB, Samant SD (2007) Synth
Commun 37:1965
26. Kassaee MZ, Rostamizadeh S, Shadjou N, Motamedi E,
Esmaeelzadeh M (2010) J Heterocycl Chem 47:1421
27. Zhang ZH, Lu HY, Yang SH, Gao JW (2010) J Comb Chem
12:643
28. Saffar-Teluri A, Bolouk S (2010) Monatsh Chem 141:1113
29. Rostamizadeh S, Amani AM, Mahdavinia GH, Sepehrian H,
Ebrahimi S (2010) Synthesis 1356
References
1. Sadanandam YS, Reddy KRM, Rao AB (1987) Eur J Med Chem
22:169
2. Hamel E, Lin CM, Plowman J, Wang HK, Lee KH, Paull KD
(1996) Biochem Pharmacol 51:53
30. Niknam K, Jafarpour N, Niknam E (2011) Chin Chem Lett 22:69
31. Wang M, Song ZG, Gong H, Jiang H (2008) Synth Commun
38:961
32. Wang M, Song ZG, Gong H, Jiang H (2008) Monatsh Chem
139:601
3. Hour MJ, Huang LJ, Kuo SC, Xia Y, Bastow K, Nakanishi Y,
Hamel E, Lee KH (2000) J Med Chem 43:4479
4. Alaimo RJ, Russell HE (1972) J Med Chem 15:335
5. Parish HA, Gilliom RD, Purcell WP, Browne RK, Spirk RF,
White HD (1982) J Med Chem 25:98
33. Wang M, Liang Y (2011) Monatsh Chem 142:153
34. Wang M, Wang ZC, Sun ZL, Jiang H (2005) Transition Met
Chem 30:792
35. Wang M, Zhang TT, Song ZG (2011) Chin Chem Lett 22:427
36. Cai GP, Xu XL, Li ZF, Weber WP, Lu P (2002) J Heterocycl
Chem 39:1271
6. Bakavoli M, Sabzevari O, Rahimizadeh M (2007) Chin Chem
Lett 18:1466
7. Jiang JB, Hesson DP, Dusak BA, Dexter DL, Kang GJ, Hamel E
(1990) J Med Chem 33:1721
8. Hattori K, Kido Y, Yamamoto H, Ishida J, Kamijo K, Murano K,
Ohkubo M, Kinoshita T, Iwashita A, Mihara K, Yamazaki S,
Matsuoka N, Teramura Y, Miyake H (2004) J Med Chem
47:4151
37. Yale HL, Kalkstein M (1967) J Med Chem 10:334
123