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Volumn 20, Issue 10, 2009, Pages 1201-1203

The simple synthesis of quinazoline-2,4-dione derivatives using Boc strategy

Author keywords

Boc strategy; Carbonylation; Cyclization; Quinazolinediones

Indexed keywords

EID: 68749117402 PISSN: 10018417 EISSN: None Source Type: Journal
DOI: 10.1016/j.cclet.2009.05.001 Document Type: Article

Times cited : (10)

References (15)

1
- 26844495371
- Michael J.P. Nat. Prod. Rep. 22 (2005) 627
- (2005) Nat. Prod. Rep. , vol.22 , pp. 627
- Michael, J.P.¹

2
- 8544247943
- Vogue M.M., and Marzinzik A.L. QSAR Comb. Sci. 23 (2004) 440
- (2004) QSAR Comb. Sci. , vol.23 , pp. 440
- Vogue, M.M.¹ Marzinzik, A.L.²

3
- 23844442559
- Connolly T.J., McGary P., and Sukhtankar S. Green Chem. 7 (2005) 586
- (2005) Green Chem. , vol.7 , pp. 586
- Connolly, T.J.¹ McGary, P.² Sukhtankar, S.³

4
- 4444357002
- Mizuno T., Iwai T., and Ishino Y. Tetrahedron Lett. 45 (2004) 7073
- (2004) Tetrahedron Lett. , vol.45 , pp. 7073
- Mizuno, T.¹ Iwai, T.² Ishino, Y.³

5
- 34547762176
- Shi D.Q., Dou G.L., Li Z.Y., et al. Tetrahedron 63 (2007) 9764
- (2007) Tetrahedron , vol.63 , pp. 9764
- Shi, D.Q.¹ Dou, G.L.² Li, Z.Y.³

6
- 3242811179
- Rivero I.A., Espinoza K., and Somanathan R. Molecules 9 (2004) 609
- (2004) Molecules , vol.9 , pp. 609
- Rivero, I.A.¹ Espinoza, K.² Somanathan, R.³

7
- 0038721776
- Okuzumi T., Nakanishi E., Tsuji T., et al. Tetrahedron 59 (2003) 5603
- (2003) Tetrahedron , vol.59 , pp. 5603
- Okuzumi, T.¹ Nakanishi, E.² Tsuji, T.³

8
- 0036304648
- Boyles D.C., Curran T.T., and Parlett R.V. Org. Process Res. Dev. 6 (2002) 230
- (2002) Org. Process Res. Dev. , vol.6 , pp. 230
- Boyles, D.C.¹ Curran, T.T.² Parlett, R.V.³

9
- 33749328794
- Colotta V., Catarzi D., Varano F., et al. J. Med. Chem. 49 (2006) 6015
- (2006) J. Med. Chem. , vol.49 , pp. 6015
- Colotta, V.¹ Catarzi, D.² Varano, F.³

10
- 49849092493
- Kuryazov R.Sh., Mukhamedov N.S., and Shakhidoyatov Kh.M. Chem. Heterocycl. Compd. 44 (2008) 324
- (2008) Chem. Heterocycl. Compd. , vol.44 , pp. 324
- Kuryazov, R.Sh.¹ Mukhamedov, N.S.² Shakhidoyatov, Kh.M.³

11
- 1842740287
- Colotta V., Catarzi D., Varano F., et al. Bioorg. Med. Chem. Lett. 14 (2004) 2345
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 2345
- Colotta, V.¹ Catarzi, D.² Varano, F.³

12
- 0030576328
- Smith A.L., Thomson C.G., and Leeson P.D. Bioorg. Med. Chem. Lett. 6 (1996) 1483
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1483
- Smith, A.L.¹ Thomson, C.G.² Leeson, P.D.³

13
- 34250626127
- Egger M., Li X.Q., Müller C., et al. Eur. J. Org. Chem. 16 (2007) 2643
- (2007) Eur. J. Org. Chem. , vol.16 , pp. 2643
- Egger, M.¹ Li, X.Q.² Müller, C.³

14
- 68749119716
- 6-Bromo-3-{4-[2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]phenyl}-1H,3H-quinazoline-2,4-dione (3a, mp 278-279 °C; 1H NMR (600 MHz, DMSO, δ ppm, 11.66 (brs, 1H, NH, 7.97 (d, 1H, J, 2.3 Hz, 7.84 (dd, 1H, J, 8.7, 2.3 Hz, 7.17 (d, 1H, J, 2.3 Hz, 7.35 (d, 2H, J, 8.3 Hz, 7.20 (d, 2H, J, 8.3 Hz, 6.65 (s, 1H, 6.64 (s, 1H, 3.69 (s, 3H, OMe, 3.68 (s, 3H, OMe, 3.56 (s, 2H, 2.61-2.89 (m, 8H, 13C NMR (150 MHz, DMSO, δ ppm, 161.19 (C, 149.99 (C, 147.13 (C, 146.89 (C, 140.61 (C, 139.00 (C, 137.90 (CH, 133.21 (C, 129.41 (CH, 129.08 (2CH, 128.64 (2CH, 126.62 (C, 125.90 (C, 117.66 (CH, 116.19 (C, 113.87 (C, 111.80 (CH, 110.02 (CH, 59.32 (CH2, 55.48 (CH3, 55.46 (CH3, 55.05 (CH2, 50.59 (CH2, 32.54 (CH2, 28.26 (CH2, ESI-MS m/z, 536.1 (M+H, 100, 538.1 98
- 2). ESI-MS m/z (%): 536.1 (M+H, 100), 538.1 (98).

15
- 68749097235
- General experimental procedure for preparing quinazolinediones 3a-d: substituted anthranilamide 1a-d (20 mmol) was dissolved in anhydrous dichloromethane (CH2Cl2, 150 mL, followed by the addition of Na2CO3 (2.36 g, 22 mmol, di-tert-butyl dicarbonate (4.85 g, 22 mmol) and the solution was stirred at room temperature for 1 h under nitrogen gas, and then heated at reflux temperature for 2 h, When the reaction was complete, the mixture was washed with water. And this solution was washed successively with 1 mol/L citric acid solution and saturated salt solution. The organic phase was dried over sodium sulfate and evaporated in vacuo. A precipitate was obtained, collected, and dried, then separated by column to provide 2a-d. Sodium methoxide (2.16 g, 40 mmol) was added with stirring at room temperature to a solution of anthranilamide 2a-d (20 mmol) in DMF 20 mL, The resulting mixture was stirred for 30 min and then heated to 80 °C under nit
- 4. Evaporation of the solvent and purification of the crude product by flash chromatography on silica gel gave 3a-d as a white solid.

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