Beilstein J. Org. Chem. 2010, 6, 1056–1060.
9. Jiarong, L.; Xian, C.; Daxin, S.; Shuling, M.; Qing, L.; Qi, Z.;
Conclusion
10.Li, Z.; Huang, H.; Sun, H.; Jiang, H.; Liu, H. J. Comb. Chem. 2008, 10,
The cyclocondensation of ethoxymethylene thiobarbituric acids
with active methylene compounds under the above noted
catalytic system, resulted in a new method for the formation of
quinazoline derivatives. Thus, the reaction of 5-ethoxymethyl-
enepyrimidine-4,6-diones 1 with malononitrile and ethyl cyano-
acetate gave 7-amino-2,3-dihydro-2-thioxo-1,3-diarylquina-
zolin-4(1H)-ones 2 and 7-hydroxy-2,3-dihydro-2-thioxo-1,3-
diarylquinozolin-4(1H)-ones 3, respectively. This new proce-
dure avoids the use of toxic reagents which are traditionally
used for the preparation of quinazolines.
11.Patil, Y. P.; Tambade, P. J.; Parghi, K. D.; Jayaram, R. V.;
Bhanage, B. M. Catal. Lett 2009, 133, 201–208.
12.Couture, A.; Cornet, H.; Grandclaudon, P. Synthesis 1991, 1009–1010.
13.Kotsuki, H.; Sakai, H.; Morimoto, H.; Suenaga, H. Synlett 1999,
14.Abdel-Jalil, R. L.; Voelter, W.; Saeed, M. Tetrahedron Lett. 2004, 45,
15.Feldman, J. R.; Wagner, E. C. J. Org. Chem. 1942, 7, 31–47.
Supporting Information
16.Yale, H. L. J. Heterocycl. Chem. 1977, 14, 1357–1359.
Supporting Information File 1
Experimental part.
17.Mhaske, S. B.; Argade, N. P. J. Org. Chem. 2004, 69, 4563–4566.
18.Saeed, A.; Shaheen, U.; Bolte, M. J. Chin. Chem. Soc. 2010, 57,
82–88.
19.Makino, S.; Suzuki, N.; Nakanishi, E.; Tsuji, T. Tetrahedron Lett. 2000,
20.Makino, S.; Nakanishi, E.; Tsuji, T. Tetrahedron Lett. 2001, 42,
21.Makino, S.; Nakanishi, E.; Tsuji, T. Bull. Korean Chem. Soc. 2003, 24,
Supporting Information File 2
IR and NMR spectra.
Supporting Information feature copies of IR and 1H NMR
spectra of
22.Ivachtchenko, A. V.; Kovalenko, S. M.; Drushlyak, O. G.
23.Devi, N. A.; Laitonjam, W. S. Indian J. Chem. 1994, 33B, 1091–1092.
24.Devi, N. A.; Laitonjam, W. S. Indian J. Heterocycl. Chem. 1995, 5,
139–140.
7-amino-2,3-dihydro-2-thioxo-1,3-di(2-methoxyphenyl)-
quinazolin-4(1H)-one (2c) and 1H and 13C NMR spectra of
7-hydroxy-2,3-dihydro-2-thioxo-1,3-di(2-methylphenyl)-
quinazolin-4(1H)-one (3a).
25.Devi, N. A.; Laitonjam, W. S. Indian J. Chem. 1996, 35B, 478–479.
26.Devi, N. A.; Khuman, C. K.; Singh, R. K. T.; Laitonjam, W. S.
Indian J. Heterocycl. Chem. 1998, 7, 193–196.
27.Thokchom, H. S.; Devi, N. A.; Laitonjam, W. S. Can. J. Chem. 2005,
Acknowledgements
28.Laitonjam, W. S.; Rajkumar, T. S.; Chingakham, B. S. Steroids 2002,
29.Tombisana, R. K.; Laitonjam, W. S. Indian J. Chem. 1999, 38B,
847–849.
The authors thank SAIF, NEHU, Shillong for taking NMR
spectral data.
30.Green, B.; Khaidem, I. S.; Crane, R. I.; Newaz, S. S. Tetrahedron 1976,
31.Khaidem, I. S.; Sagolsem, L. S.; Laishram, R. S.; Khan, M. Z. R.
Indian J. Chem. 1996, 35B, 911–914.
References
1. Connolly, D. J.; Cusack, D.; O’Sullivian, T. P.; Guiry, P. J. Tetrahedron
2. Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787–9826.
32.Ghosh, A. K.; Bilcer, G.; Schiltz, G. Synthesis 2001, 2203–2229.
3. Xia, Y.; Yang, Z.-Y.; Hour, M.-J.; Kuo, S.-C.; Xia, P.; Bastow, K. F.;
Nakanishi, Y.; Nampoothiri, P.; Hackl, T.; Hamel, E.; Lee, K.-H.
Bioorg. Med. Chem. Lett. 2001, 11, 1193–1196.
33.List, B.; Castello, C. Synlett 2001, 1687–1689.
4. De Clercq, E. Curr. Med. Chem. 2001, 8, 1543–1572.
5. Corbett, J. W. Curr. Med. Chem. - Anti-Infect. Agents 2002, 1,
119–140.
6. LeMahieu, R. A.; Carson, M.; Welton, A. F.; Baruth, H. W.; Yaremko, B.
7. Vandenberk, J.; Kennis, L.; Van der Aa, M.; Van Heertum, A. U.S.
Patent 4, 522, 945, June 11, 1985.
8. Sohda, T.; Makino, H.; Baba, A. Eur. Patent EP0567107, Oct 27, 1993.
1059