Abstract
The effect of substituents on the intramolecular cyclization of 2-hydroxycinnamaldehydes was studied. It was established that aldehydes that contain bulky groups in the side chain and in the 3 position of the benzene ring are readily converted to intramolecular hemiacetals or bimolecular acetals either spontaneously at the moment of isolation or in solutions in DMF or DMSO, as well as on heating. An increase in the lability of the phenolic proton favors the cyclization.
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E. A. Medyantseva, O. M. Babeshko, and V. I. Minkin, Zh. Org. Khim., 12, 897 (1976).
O. M. Babeshko, E. A. Medyantseva, O. T. Lyashik, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 11, 1477 (1982).
I. M. Andreeva, O. M. Babeshko, E. A. Medyantseva, and V. I. Minkin, Zh. Org. Khim., 15, 1899 (1979).
I. M. Andreeva, O. M. Babeshko, E. M. Bondarenko, I. A. Barchan, O. T. Lyashik, E. A. Medyantseva, and Yu. N. Simkina, Khim.-farm. Zh., 19, 177 (1985).
I. M. Andreeva, E. M. Bondarenko, E. A. Medyantseva, R. G. Pudeyan, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 5, 610 (1982).
I. M. Andreeva, E. M. Bondarenko, E. A. Medyantseva, and V. I. Minkin, Khim. Geterotsikl. Soedin., No. 2, 181 (1983).
R. É. Valter, Ring-Chain Isomerism in Organic Chemistry [in Russian], Zinatne, Riga (1978).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 460–465, April, 1988.
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Chunaev, Y.M., Przhiyalgovskaya, N.M. & Kurkovskaya, L.N. Intramolecular cyclization of 2-hydroxycinnamaldehydes. Chem Heterocycl Compd 24, 376–381 (1988). https://doi.org/10.1007/BF00478854
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DOI: https://doi.org/10.1007/BF00478854