Abstract
Dyes that absorb at 525–580 nm were obtained by the reaction of derivatives of 1,3-dithiolium iodide (or perchlorate) with 1-phenyl-3,5-di-R-2-pyrazolines, N,N-dimethylaniline, and benzaldehyde N-methylphenylhydrazone. It was demonstrated by alternative synthesis that the reaction takes place in the para position of the N-phenyl group. Dyes can be obtained in two steps from 2-dimethylamino-1,3-dithioles and activated aromatic compounds with subsequent oxidation of the intermediate leuco compounds with air oxygen.
Article PDF
Similar content being viewed by others
Literature cited
E. Campaigne and R. D. Hamilton, Quart. Rep. Sulfur Chem., 5, 275 (1970).
M. Narita and C. U. Pittman, Jr., Synthesis, No. 8, 489 (1976).
J. Nakayama, K. Fujiwara, and M. Hoshino, Bull. Chem. Soc. Jpn., 49, 3567 (1976).
J. Nakayama, Synthesis, No. 3, 171 (1975).
V. D. Orlov and A. I. Roberman, Dokl. Akad. Nauk SSSR, 246, 888 (1979).
V. D. Orlov, A. I. Roberman, A. I. Rybachenko, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., No. 11, 1538 (1977).
A. F. Plue, U.S. Patent No. 2976295; Chem. Abstr., 55, 16569 (1961).
L. A. Kutulya, A. E. Shevchenko, and Yu. N. Surov, Khim. Geterotsikl. Soedin., No. 2, 250 (1975).
G. F. Duffin and J. D. Kendall, J. Chem. Soc., No. 1, 408 (1954).
L. Szucs and A. Bradlerova, Z. Chem., 15, 477 (1975).
J. Nakayama, Synthesis, No. 1, 38 (1975).
J. Degani and R. Fochi, J. Chem. Soc., Perkin Trans. I, No. 17, 1886 (1976).
A. V. Luzanov, A. A. Sukhorukov, and V. É. Umanskii, Teor. Éksp. Khim., 10, 456 (1974).
L. A. Kutulya, V. F. Morina, A. E. Shevchenko, and Yu. N. Surov, Zh. Prikl. Khim., 27, 76 (1977).
E. Campaigne and R. D. Hamilton, J. Org. Chem., 29, 1711 (1964).
K. Hirai, Tetrahedron, 27, 4003 (1971).
R. Zahradnik and R. Polak, Fundamentals of Quantum Chemistry [Russian translation], Mir, Moscow (1977), p. 230.
E. Faughanel, J. Prakt. Chem., 317, 123 (1975).
E. Campaigne and N. W. Jacobsen, J. Org. Chem., 29, 1703 (1964).
K. M. Pazdro and W. Polaczkowa, Rocz. Chem., 45, 811 (1971).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1245–1250, September, 1981.
Rights and permissions
About this article
Cite this article
Gella, I.M., Vakula, V.N. & Orlov, V.D. Electrophilic substitution in n-aryl-2-pyrazolines: Reactions with 1,3-dithioles. Chem Heterocycl Compd 17, 932–936 (1981). https://doi.org/10.1007/BF00505601
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00505601