Abstract
We have demonstrated the basic possibility of cyclizing guanidinoalkanethiols of different structure to thiazolines and thiazines. The rate of reaction depends on the pH of the medium. The concentration of buffer and the addition of heavy water and α-D,L-alanine have virtually no effect on the rate of reaction.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
Literature Cited
A. Shöberl and G. Hanser, Berichte, 91, 1239 (1958).
R. Shapira, D. G. Doherty, and W. T. Burnett, Radiat. Res., 7, 22 (1957).
R. Burnett and W. P. Jencks, J. Am. Chem. Soc., 90, 199 (1968).
J. X. Khum, R. Shapira, and D. G. Doherty, J. Am. Chem. Soc., 79, 5563 (1957).
D. G. Doherty, R. Shapira, and W. T. Burnett, J. Am. Chem. Soc., 79, 5567 (1957).
J. X. Khum, D. G. Doherty, and R. Shapira, J. Am. Chem. Soc., 80, 3342 (1958).
D. G. Doherty and R. Shapira, J. Org. Chem., 28, 1339 (1963).
W. O. Foye, T. Mickels, R. N. Duval, and T. R. Marshall, J. Med. Chem., 6, 509 (1963).
K. Doerfel, Statistics in Analytical Chemistry [Russian translation], Mir, Moscow (1969), p. 93.
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1572–1575, November, 1987.
Rights and permissions
About this article
Cite this article
Mandrugin, A.A., Fedoseev, V.M., Khomutov, S.M. et al. Intramolecular cyclization of guanidinoalkanethiols in aqueous solution. Chem Heterocycl Compd 23, 1262–1266 (1987). https://doi.org/10.1007/BF00479384
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00479384