Abstract
The reaction between p-(dimethylamino)benzaldehyde and 2-acylmethyl-1H-benzimidazoles and 6-amino-1,3-dimethylpyrimidino-2,4(1H,3H)-dione has given previously unknown 5-unsubstituted 6-(1H-benzimidazol-2-yl)pyrido[2,3-d]pyrimidino-2,4(1H,3H)-diones. The reaction occurs on boiling in acetic and acid and includes the formation of 1,4-dihydropyridine-bearing compounds in accordance with the Hantzsch reaction scheme and aromatization as a result of cleavage of N,N-dimethylaniline.
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References
K. V. Vatsuro and G. L. Mishchenko, Named Reactions in Organic Chemistry [in Russian], Khimiya, Moscow (1976).
F. E. Sausin’sh and G. Ya. Dubur, Khim. Geterotsikl. Soed., 435 (1992) [Chem. Heterocycl. Comp., 28, 363 (1992)].
I. B. Dzvinchuk and N. A. Tolmacheva, Khim. Geterotsikl. Soed., 554 (2001) [Chem. Heterocycl. Comp., 37, 506 (2001)].
A. Agarwal and P. M. S. Chauhan, Tetrahedron Lett., 46, 1345 (2005).
A. Agarwal and P. M. S. Chauhan, Synth. Commun., 34, 4447 (2004).
U. Girreser, D. Heber, and M. Schuett, Tetrahedron, 60, 11511 (2004).
M. Takahashi, H. Nagaoka, and K. Inoue, J. Heterocycl. Chem., 41, 525 (2004).
I. Devi and P. J. Bhuyan, Synlett, 283 (2004).
E. C. Taylor and B. Bhatia, Heterocycles, 61, 113 (2003).
I. Devi, B. S. D. Kumar, and P. J. Bhuyan, Tetrahedron Lett., 44, 8307 (2003).
D. M. Volochnyuk, A. O. Pushechnikov, D. G. Krotko, D. A. Sibgatulin, S. A. Kovalyova, and A. A. Tolmachev, Synthesis, 10, 1531 (2003).
T. Kuwada, K. Harada, J. Nobuhiro, T. Choshi, and S. Hibino, Heterocycles, 57, 2081 (2002).
D. D. Hughes and M. C. Bagley, Synlett, 1332 (2002).
R. B. Nicewonger, L. Ditto, D. Kerr, and L. Varady, Bioorg. Med. Chem. Lett., 12, 1799 (2002).
M. Nitta and H. Kanda, Heterocycles, 57, 491 (2002).
N. Rosas, P. Sharma, C. Alvarez, A. Cabrera, R. Ramires, A. Delgado, and H. Arzoumanian, J. Chem. Soc., Perkin Trans. 1, 19, 2341 (2001).
A. A. S. El-Ahl, S. A. A. E. Bialy, and M. A. Ismail, Heterocycles, 55, 1315 (2001).
P. Srivastava, A. S. Saxena, and V. J. Ram, Synthesis, 541 (2000).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 585–589, April 2007.
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Dzvinchuk, I.B., Lozinskii, M.O. The p-(dimethylamino)benzaldehyde modification of Hantzsch reaction: Synthesis of 6-(1H-benzimidazol-2-yl)pyrido[2,3-d]pyrimidino-2,4(1H, 3H)-diones. Chem Heterocycl Compd 43, 480–484 (2007). https://doi.org/10.1007/s10593-007-0069-y
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DOI: https://doi.org/10.1007/s10593-007-0069-y