Abstract
The corresponding 5-aroyl derivatives were obtained by reaction of aromatic carboxylic acid chlorides with 3-ethylrhodanine, and their chemical and physicochemical properties were studied. It is shown that they are completely enolized and stabilized by intramolecular hydrogen bonding; the side-chain carbonyl group undergoes enolization. Methylation with diazomethane gives O-ethers α-methoxyarylidene derivatives of 3-ethylrhodanine and S-ethers, which exist as dipolar ions.
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Literature cited
A. Albert and E. Serjeant, lonization Constants of Acids and Bases, Methuen (1962).
N. M. Turkevich and I. I. Kurnitskii, Ukr. Khim. Zh., 16, 454 (1950).
I. Ya. Kvitko and B. A. Porai-Koshits, Zh. Organ. Khim., 2, 169 (1966).
A. E. Lutskii, Zh. Obshch. Khim., 14, 487 (1944).
S. Abrahamsson and A. Westerdahl, Acta Chem. Scand., 21, 442 (1967).
C. P. Lo and W. J. Croxall, J. Am. Chem. Soc., 76, 4166 (1954).
C. P. Lo, J. Am. Chem. Soc., 80, 3466 (1958).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1491–1495, November, 1972.
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Kvitko, I.Y., Bolkhovets, S.V. & Kokurina, A.M. C-Acylation of rhodanine derivatives. Chem Heterocycl Compd 8, 1345–1349 (1972). https://doi.org/10.1007/BF00471868
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DOI: https://doi.org/10.1007/BF00471868