K. Karnakar et al. / Tetrahedron Letters 53 (2012) 4613–4617
4617
4. Kabri, Y.; Azas, N.; Dumetre, A.; Hutter, S.; Laget, M.; Verhaeghe, P.; Gellis, A.;
Vanelle, P. Eur. J. Med. Chem. 2010, 45, 616–622.
5. Kumar, A.; Sharma, P.; Kumari, P.; Kalal, B. L. Bioorg. Med. Chem. Lett. 2011, 21,
4353–4357.
6. Yoshida, S.; Aoyagi, T.; Harada, S.; Matsuda, N.; Ikeda, T.; Naganawa, H.;
Hamada, M.; Takeuchi, T. J. Antibiot. 1991, 44, 111.
7. Wattanapiromsakul, C.; Forster, P. I.; Waterman, P. G. Phytochemistry 2003, 64,
609.
20. Kumar, A. V.; Rao, K. R. Tetrahedron Lett. 2011, 52, 5188.
21. Karnakar, K.; Shankar, J.; Murthy, S. N.; Ramesh, K.; Nageswar, Y. V. D. Synlett
2011, 1089.
22. (a) Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K. R.; Nageswar, Y. V. D. Helv
Chim. Acta. 2009, 92, 2118; (b) Murthy, S. N.; Madhav, B.; Kumar, A. V.; Rao, K.
R.; Nageswar, Y. V. D. Tetrahedron 2009, 65, 5251; (c) Madhav, B.; Murthy, S. N.;
Reddy, V. P.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron Lett. 2009, 50, 6025; (d)
Murthy, S. N.; Madhav, B.; Reddy, V. P.; Nageswar, Y. V. D. Tetrahedron Lett.
2010, 51, 3649; (e) Shankar, J.; Karnakar, K.; Srinivas, B.; Nageswar, Y. V. D.
Tetrahedron Lett. 2010, 51, 3938; (f) Murthy, S. N.; Madhav, B.; Nageswar, Y. V.
D. Tetrahedron Lett. 2010, 51, 5252; (g) Ramesh, K.; Murthy, S. N.; Nageswar, Y.
V. D. Tetrahedron Lett. 2011, 52, 2362; (h) Anil Kumar, B. S. P.; Madhav, B.;
Harsha Vardhan Reddy, K.; Nageswar, Y. V. D. Tetrahedron Lett. 2011, 52, 2862.
23. General procedure for the synthesis of 2-phenylquinazolines: To a magnetically
stirred 2-amino benzo/acetophenone (1.0 mmol) in acetonitrile (10 mL),
benzylamine (2.5 mmol), graphite oxide 10 wt % (with respect to 2-amino
8. Deng, Y.; Xu, R.; Ye, Y. J. Chin. Pharm. Sci. 2000, 9, 116.
9. Ma, Z.-Z.; Hano, Y.; Nomura, T.; Chen, Y.-J. Heterocycles 1997, 46, 541.
10. (a) Ple, P. A.; Green, T. P.; Hennequin, L. F.; Curwen, J.; Fennell, M.; Allen, J.;
Lambert-van der Brempt, C.; Costello, G. J. Med. Chem. 2004, 47, 871; (b)
Boyapati, S.; Kulandaivelu, U.; Sangu, S.; Vanga, M. R. Arch. Pharm. 2010, 343,
570–576; (c) Yang, S. H.; Khadka, D. B.; Cho, S. H.; Ju, H. K.; Lee, K. Y.; Han, H. J.;
Lee, K. T.; Cho, W. J. Bioorg. Med. Chem. 2011, 19, 968–977; (d) Kim, Y. H.; Choi,
H.; Lee, J.; Hwang, I. C.; Moon, S. K.; Kim, S. J.; Lee, H. W.; Im, D. S.; Lee, S. S.;
Ahn, S. K.; Kim, S. W.; Han, C. K.; Yoon, J. H.; Lee, K. J.; Choi, N. S. Bioorg. Med.
Chem. Lett. 2008, 18, 6279–6282.
11. (a) Li, J. R.; Chen, X.; Shi, D. X.; Ma, S. L.; Li, Q.; Zhang, Q.; Tang, J. H. Org. Lett.
2009, 11, 1193; (b) Connolly, D. J.; Cusack, D.; OSullivan, T. P.; Guiry, P. J.
Tetrahedron 2005, 61, 10153; (c) Witt, A.; Bergman, J. Curr. Org. Chem. 2003, 7,
659.
12. Kotsuki, H.; Sakai, H.; Morimoto, H.; Suenaga, H. Synlett 1999, 1993–1995.
13. (a) Truong, V. L.; Marrow, M. Tetrahedron Lett. 2010, 51, 758–760; (b) Qiu, D.;
Mo, F. Y.; Zheng, Z. T.; Zhang, Y.; Wang, J. B. Org. Lett. 2010, 12, 5474–5477.
14. (a) Zhang, J. T.; Zhu, D. P.; Yu, C. M.; Wan, C. F.; Wang, Z. Y. Org. Lett. 2010, 12,
2841–2843; (b) Han, B.; Wang, C.; Han, R. F.; Yu, W.; Duan, X. Y.; Fang, R.; Yang,
X. L. Chem. Commun. 2011, 47, 7818–7820; (c) Zhang, J. T.; Yu, C. M.; Wang, S. J.;
Wan, C. F.; Wang, Z. Y. Chem. Commun. 2010, 46, 5244–5246.
15. Anand, N.; Reddy, K. H. P.; Satyanarayana, T.; Rao, K. S. R.; Raju, D. B. Catal. Sci.
Technol. 2012, 2, 570–574.
benzo/acetophenone), and TBHP (200 lL of 70 % aqueous solution) were added
at 70–75 ° C until the reaction goes for completion as indicated by TLC. After
completion of the reaction, the catalyst was separated by filtration and washed
with water for reuse. The reaction mixture was concentrated to remove
acetonitrile. After evaporation of the solvent under reduced pressure, the crude
residue was extracted with ethylacetate and the combined organic layers were
washed with brine solution, dried over anhydrous Na2SO4, evaporated to get
crude product and purified by column chromatography by using hexane and
ethylacetate (9:1) as eluent to give the titled compound 2-phenylquinazoline.
24. Data for representative examples
2,4-Diphenylquinazoline (Table 1, entry 1)14: Yellow solid, mp 118–120 °C. 1
H
NMR (300 MHz, CDCl3, TMS) d = 8.67–8.70 (m, 2H), 8.11 (t, J = 8.3 Hz, 2H),
7.82–7.88 (m, 3H), 7.48–7.58 (m, 7H) ppm. 13C NMR (75 MHz CDCl3, TMS) d
121.7, 126.9, 128.4, 128.7, 129.2, 129.8, 130.2, 130.4, 133.4, 137.7, 138.1, 152.0,
160.2, 168.2 ppm. ESI-MS: 283 (M+H)+; C20H14N2.
16. Zhang, Z.-H.; Zhang, X.-N.; Mo, L.-P.; Li, Y.-X.; Ma, F.-P. Green Chem. doi: http://
2-(4-Methoxyphenyl)-4-phenylquinazoline (Table 1, entry 2)14: Brown solid,
mp 159–162 °C. 1H NMR (300 MHz, CDCl3, TMS) d = 8.11–8.17 (m, 2H), 7.81–
7.90 (m, 4H), 7.53–7.56 (m, 4H) 7.37–7.43 (m, 1H), 7.01–7.09 (m, 2H) 3.89 (s,
3H) ppm. 13C NMR (75 MHz CDCl3, TMS) d 55.3, 113.8, 121.8, 125.7, 128.6,
128.9, 129.9, 130.1, 130.3, 130.5, 132.0, 133.9, 134.3, 137.1, 150.4, 160.1, 161.9,
167.3 ppm. ESI-MS: 313 (M+H)+; C21H16N2O.
17. (a) Hara, M.; Yoshida, T.; Takagaki, A.; Takata, T.; Kondo, J. N.; Hayashi, S.;
Domen, K. Angew. Chem. 2004, 116, 3015–3018. Angew. Chem., Int. Ed., 2004, 43,
2955–2958; (b) Toda, M.; Takagaki, A.; Okamura, M.; Kondo, J. N.; Hayashi, S.;
Domen, K.; Hara, M. Nature 2005, 438, 178; (c) Takagaki, A.; Toda, M.; Okamura,
M.; Kondo, J. N.; Hayashi, S.; Domen, K.; Hara, M. Catal. Today 2006, 116, 157–
161; (d) Zong, M. H.; Duan, Z. Q.; Lou, W. Y.; Smith, T. J.; Wu, H. Green Chem.
2007, 9, 434–437.
18. (a) Dreyer, D. R.; Jia, H.-P.; Bielawski, C. W. Angew. Chem. 2010, 121, 6965–
6968. Angew. Chem., Int. Ed. 2010, 49, 6813–6816; (b) Jia, H.-P.; Dreyer, D. R.;
Bielawski, C. W. Tetrahedron 2011, 67, 4431–4434; (c) Jia, H.-P.; Dreyer, D. R.;
Bielawski, C. W. Adv. Synth. Catal. 2011, 353, 528; (d) Dreyer, D. R.; Bielawski, C.
W. Chem. Sci. 2011, 2, 1233–1240.
8-Methyl-6-phenyl-[1,3]dioxolo [4, 5-g] quinazoline (Table 2, entry 1)21
:
Brown solid, mp 132–135 °C. 1H NMR (300 MHz, CDCl3, TMS) d = 8.52 (d,
J = 7.9 Hz, 2H), 7.46–7.49 (m, 3H), 7.29 (s, 1H), 7.22 (s, 1H), 6.08 (s, 2H), 2.84 (s,
3H) ppm. 13C NMR (75 MHz CDCl3, TMS) d 22.0, 100.1, 101.9, 105.3, 119.5,
128.1, 128.3, 129.9, 138.3, 147.8, 149.7, 153.2, 159.1, 165.0 ppm. ESI-MS: 265
(M+H)+; C16H13N2O2.
6-(4-Methoxyphenyl)-8-methyl-[1,3]dioxolo [4, 5-g] quinazoline (Table 2,
entry 2)21: Brown solid, mp 138–142 °C. 1H NMR (300 MHz, CDCl3, TMS)
d = 8.50 (d, J = 8.8 Hz, 2H), 7.26–7.30 (m, 2H), 7.01 (d, J = 9.0 Hz, 2H), 6.13 (s,
2H), 6.08 (s, 2H), 3.88 (s, 3H), 2.86 (s, 3H) ppm. 13C NMR (75 MHz CDCl3, TMS) d
22.0, 55.1, 101.2, 102.0, 105.0, 120.2, 128.0, 128.3, 130.0, 138.0, 148.2, 149.7,
153.2, 159.1, 165.0 ppm. ESI-MS: 295 (M+H)+; C17H15N2O3.
19. (a) Hummers, W. S., Jr.; Offeman, R. E. J. Am. Chem. Soc. 1958, 80, 1339; (b)
Staudenmaier, L. Ber. Dtsch. Chem. Ges. 1898, 31, 1481; (c) Staudenmaier, L. Ber.
Dtsch. Chem. Ges. 1899, 32, 1394; (d) Nakajima, T.; Matsuo, Y. Carbon 1994, 32,
469.