Substituted 2-spiropyrimidin-4-ones are formylated at room temperature under the conditions of the Vilsmeier–Haack reaction. When cautiously heated they undergo electrophilic rearrangement.
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W. Su, Y. Weng, L. Jiang, Y. Yang, L. Zhao, Z. Chen, Z. Li, and J. Li, Org. Prep. Proced. Int., 42, 503 (2010).
Q. Li, L. A. Mitscher, and L. L. Shen, Med. Res. Rev., 20, 231 (2000).
M. Nagarajan, X. Xiao, S. Antony, G. Kohlhagen, Y. Pommier, and M. Cushman, J. Med. Chem., 46, 5712 (2003).
V. I. Markov, O. K. Farat, S. A. Varenichenko, and E. V. Velikaya, Mendeleev Commun., 22, 101 (2012).
R. Crossley and R. G. Shepherd, J. Chem. Soc., Perkin Trans. 1, 2479 (1985).
V. I. Markov, O. K. Farat, S. A. Varenichenko, E. V. Velikaya, R. I. Zubatyuk, and O. V. Shishkin, Chem. Heterocycl. Compd., 49, 1158 (2013). [Khim. Geterotsikl. Soedinenii, 1244 (2013)].
C. Bischoff, E. Schröder, and E. Gründemann, J. Prakt. Chem., 326, 849 (1984).
G. Zigeuner, W. Adam, and H. Weichsel, Monatsh. Chem., 97, 55 (1966).
S. Schramm, E. Schmitz, and E. Gründemann, J. Prakt. Chem., 326, 279 (1984).
V. I. Markov and Yu. Stroev, Voprosy Khimii i Khim. Tekhnologii, 3, 30 (2012).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1743–1748, November, 2014.
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Varenichenko, S.A., Farat, O.K. & Markov, V.I. Reactivity of Substituted 2-Spiropyrimidin-4-Ones Under Vilsmeier–Haack Conditions. Chem Heterocycl Comp 50, 1602–1607 (2015). https://doi.org/10.1007/s10593-014-1626-9
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DOI: https://doi.org/10.1007/s10593-014-1626-9