Abstract
The imidazolium salt, obtained by the multicomponent condensation of benzyl isonitrile, methylamine, cyclohexanone, and thiocyanic acid, undergoes thermal recyclization to 1-methyl-2-thio-4-imino-5-spirocyclohexanehydantoin. The stereochemical and structural features and properties of the 2-thiohydantoins are analyzed on the basis of the data of x-ray structural analysis and geometrical modeling.
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Literature Cited
A. I. Polyakov, L. A. Medvedeva, O. A. D'yachenko, A. B. Zolotoi, and L. O. Atovmyan, Khim. Geterotsikl. Soedin., No. 1, 53 (1986).
I. Ugi, F. K. Rosendahe, and F. Bodesheim, Annalen, 666, 54 (1963).
I. Ugi, Isonitrile Chemistry, Acad. Press, New York (1971), p. 145.
D. E. Jensen, S.-O. Laweson, R. Bardi, A. M. Piazzesi, and C. Toniolo, Tetrahedron, 41, 5595 (1985).
N. A. Tarasenko, V. P. Avakyan, and V. V. Belik, Zh. Strukt. Khim., 19, 541 (1978).
K. E. Raczyns and J. Ozczapowitz, Tetrahedron, 41, 5175 (1985).
I. D. Cunningham and A. F. Hegarty, J. Chem. Soc., Perkin Trans. 2, No. 4, 537 (1986).
S. Lifson, A. I. Hagler, and P. Dauber, J. Am. Chem. Soc., 101, 5111 (1979).
J. Uvoslef, M. L. Fracy, and C. P. Nash, Acta Cryst., C42, 353 (1986).
Yu. V. Zefirov and P. M. Zorkii, Zh. Strukt. Khim., 15, 118 (1974).
V. V. Negrebetskii, V. I. Kal'chenko, O. V. Balitskaya, M. Yu. Kornilov, and L. N. Markovskii, Zh. Obshch. Khim., 54, 1764 (1984).
Yu. N. Sheinker, Dokl. Akad. Nauk SSSR, 113, 1080 (1957).
H. B. Burgi, J. D. Danitz, and E. Shefter, Acta Cryst., B30, 1517 (1974).
V. I. Andrianov, D. Sh. Safina, and B. A. Tarnopol'skii, “Rentgen-75.” An Automated System of Programs for the Decoding of Crystal Structures [in Russian], Publishing House of the Institute of Chemical Physics of the Academy of Sciences of the USSR, Chernogolovka (1975), p. 82.
C. Giacovazzo, Acta Cryst., A30, 390 (1974).
A. N. Chekhlov, Kristallografiya, 26, 596 (1981).
Yu. A. Ustynyuk, Quantum-chemical Methods of Calculation of Molecules [in Russian], Khimiiya, Moscow (1980).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 485–492, April, 1989.
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Medvedeva, L.A., Zoloti, A.B., Polyakov, A.I. et al. Synthesis, structure, and properties of 2-thio-4-imino-5-spirocyclohexanehydantoins. Chem Heterocycl Compd 25, 403–409 (1989). https://doi.org/10.1007/BF00480753
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DOI: https://doi.org/10.1007/BF00480753