The reaction of substituted cinnamonitriles and 4-amino-2,6-dihydroxypyrimidine or 2,4-diamino-6-hydroxypyrimidine in water in the presence of triethylbenzylammonium chloride (TEBA) as catalyst affords a clean synthesis of pyrido[2,3-d]pyrimidine derivatives.
LiC.J., and ChangT. H., Organic Reactions in Aqueous MediaWiley, New York, 1997; F. Fringuell, O. Piematti, F. Pizzo and L. Vaccaro, Eur. J. Org. Chem., 2001, 439; S.C. Stinson, Chem. Eng. News, 1996, 74, 39.
3.
BreslowR., and RideoutD. C., J. Am. Chem. Soc., 1980, 102, 7816; R. Breslow, Acc. Chem. Res., 1991, 24, 59.
4.
LiC.J., Chem. Rev., 1993, 93, 2023; R. Ballini and G. Bosica, Tetrahedron Lett., 1996, 37, 8027; R. Ballini, G. Bosica and T. Mecozzi, Tetrahedron, 1997, 53, 1341; A. Meijer, S. Otto and J.B.F.N. Engberts, J. Org. Chem., 1998, 63, 8989; F. Bigi, L. Chesini, R. Maggi and G. Sartori, J. Org. Chem., 1999, 64, 1033; F. Bigi, S. Carloni, L. Ferrari, R. Maggi, A. Mazzacani and G. Sartori, Tetrahedron Lett., 2001, 42, 5203.
5.
FringuelliF., PaniG., PiermattiO., and PizzoF., Tetrahedron, 1994, 50, 1499.
6.
AndersonG.L., ShimJ. L., and BroomA. D., J. Org. Chem., 1976, 41, 1095; E.M. Grivaky, S. Lee, C.W. Siyal, D.S. Duch and C.A. Nichol, J. Med. Chem., 1980, 23, 327.
7.
FuruyaS., and OhtakiT., Eur. Pat. Appl. Ep., 608565, 1994 (Chem. Abstr., 1994, 121, 205395); D. Heber, C. Heers and U. Ravens, Pharmazie., 1993, 48, 537.
8.
SakumaY., HasegawaM., KataokaK., HoshinaK., YamazakiN., KadataT., and YamaguchiH., PCT Int. Appl., WO 9105785, 1989 (Chem. Abstr., 1991, 115, 71646).
9.
AhluwaliaV.K., BatlaR., KhuranaA., and KumarR., Ind. J. Chem., 1990, 29, 1141.
10.
ChengT., WangY., and CaiM., Chin. J. Org. Chem., 1988, 8, 250; M.R. Spada, R.S. Klein and B.A. Otter, J. Heterocyclic Chem., 1989, 26, 1851; V.K. Ahluwalia, R. Kumar, K. Khurana and R. Bhatla, Tetrahedron, 1990, 46, 3953; V.K. Ahluwalia, R. Bhatla, K. Khurana and R. Kumar, Ind. J. Chem., 1990, 29, 1141; V.K. Ahluwalia, H.R. Sharma and R. Tyagi, Tetrahedron, 1986, 42, 4045; V.K. Ahluwalia, R. Aggarwal, M. Alauddin, G. Gill and C.H. Khanduri, Heterocycles, 1990, 31, 31; A.D. Broom, J.L. Shim and C.L. Anderson, J. Org. Chem., 1976, 41, 1095; H. Wamhoff. and J. Muhr, Synthesis, 1988: 919; K. Hirota, H. Kuki and Y. Maki, Heterocycles, 1994, 37, 563; P. Srivastava, A.S. Saxena and V.J. Ram, Synthesis, 2000, 541.
11.
ShiD.Q., ChenJ., ZhuangQ. Y., WangX. S., and HuH. W., J. Chem. Res., (S), 2003, 674; J. Wang, D.Q. Shi, Q.Y. Zhuang, X.S. Wang and H.W. Hu, J. Chem. Res., (S) 2004, 818; D.Q. Shi, J. Chen, Q.Y. Zhuang, X.S. Wang and H.W. Hu, Chin. Chem. Lett., 2003, 14, 1242; D.Q. Shi, S. Zhang, Q.Y. Zhuang, X.S. Wang, S.J. Tu and H.W. Hu, Chin. J. Org. Chem., 2003, 21, 680; D.Q. Shi, Q.Y. Zhuang, J. Chen, X.S. Wang, S.J. Tu and H.W. Hu, Chin. J. Org. Chem., 2003, 23, 694; D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu and H.W. Hu, Chin. J. Org. Chem., 2003, 23, 809; D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu and H.W. Hu, Chin. J. Org. Chem., 2003, 23, 877; D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu and H.W. Hu, Chin. J. Org. Chem., 2003, 23, 1036; D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu and H.W. Hu, Chin. J. Org. Chem., 2003, 23, 1314; D.Q. Shi, J. Mou, Q.Y. Zhuang, X.S. Wang, and S.J. Tu, Chin. J. Org. Chem., 2004, 24, 1042.
