The interaction of ortho-aminoaryl polyethers, derivatives of mono-, di-, and triethylene glycol, with acetyl ketene, generated from 2,2,6-trimethyl-4H-1,3-dioxin-4-one produced acetoacetanilide- containing podands. 2,2,6-Trimethyl-4H-1,3-dioxin-4-one reacted with aminoaryl-substituted podands containing a short polyether chain (1-2 atoms) in toluene medium without catalyst. Acetoacetanilide- containing podands with longer polyether chains could be obtained by using triethylamine or acetic acid as catalyst. Acetoacetanilide-containing podands were used in the Biginelli reaction as СН-active components.
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E. S. Pereyaslavskaya, V. A. Potemkin, E. V. Bartashevich, M. A. Grishina, G. L. Rusinov, O. V. Fedorova, M. S. Zhidovinova, and I. G. Ovchinnikova, Khim.-Farm. Zh., 42, No. 11, 18 (2008). [Pharm. Chem. J., 42, 622 (2008).]
M. S. Zhidovinova, O. V. Fedorova, G. L. Rusinov, and I. G. Ovchinnikova, Mol. Diversity, 6, 323 (2003).
R. J. Clemens and J. A. Hyatt, J. Org. Chem., 50, 2431 (1985).
R. J. Clemens, Chem. Rev., 86, 241 (1986).
G. Henning, US. Pat. Appl. 3795528.
J. B. Pierce, Z. S. Ariyan, and G. S. Ovenden, J. Med. Chem., 25, 131, (1982).
O. V. Fedorova, Diss. Cand. Chem. Sci., Yekaterinburg (1990).
M. S. Zhidovinova, O. V. Fedorova, G. L. Rusinov, and I. G. Ovchinnikova, Izv. Akad. Nauk, Ser. Khim., 2389 (2003). [Russ. Chem. Bull., 52, 1768 (2003).]
F. S. Falsone and C. O. Kappe, ARKIVOC, ii, 122 (2001).
I. G. Ovchinnikova, Diss. Cand. Chem. Sci., Yekaterinburg (2007).
G. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).
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Dedicated to Academician O. N. Chupakhin on the occasion of his 80th birthday.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1083-1089, July, 2014.
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Radionova, E.S., Titova, Y.A., Isenov, M.L. et al. Diaryl-Substituted Polyethers with Acetoacet-Anilide Fragment in the Synthesis of Dihydro-Pyrimidine-Containing Podands* . Chem Heterocycl Comp 50, 998–1004 (2014). https://doi.org/10.1007/s10593-014-1555-7
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DOI: https://doi.org/10.1007/s10593-014-1555-7