Abstract
On the basis of VU and PMR spectroscopic data with the aid of the method of experimental structures and the method of dipole moments it was concluded that the products of the reaction of 1,4-dichlorophthalazine with ammonia, methylamine, and aniline in solutions and in the crystalline form exist primarily as Z conformers of the amino tautomeric form. Conversion to the tautomeric imino form was established for 1-phenylamino-4-chlorophthalazine in a number of solvents. The imines of 2-methyl-4-chlorophthalazine exist as the E isomers.
Similar content being viewed by others
Literature cited
A. R. Katritzkii, Usp. Khim., 41, 700 (1972).
L. M. Jackman and J. Timothy, J. Am. Chem. Soc., 97, 2811 (1975).
I. Satoda, F. Kusada, and K. Moroi, Yakugaku Zasshi, 82, 232 (1962); Chem. Abstr., 58, 3427 (1962).
D. Haworth and S. Robinson, J. Chem. Soc., No. 6, 777 (1948).
G. A. Elvidge and A. P. Pedman, J. Chem. Soc., Perkin Trans. I, No. 22, 2820 (1972).
Yu. N. Sheinker and Yu. I. Pomerantsev, Zh. Fiz. Khim., 30, 79 (1956).
Yu. N. Sheinker, T. V. Gortinskaya, and T. P. Sycheva, Zh. Fiz. Khim., 31, 599 (1957).
M. J. Cook, A. R. Katritzky, A. D. Page, and M. Ramiah, J. Chem. Soc., Perkin Trans. II, No. 9, 1184 (1977).
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, S. A. Flegontov, V. V. Zverev, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., No. 3, 402 (1976).
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., No. 5, 699 (1978).
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., No. 5, 690 (1978).
N. N. Bystrykh, B. I. Buzykin, A. P. Stolyarov, S. A. Flegontov, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., No. 5, 678 (1981).
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., No. 9, 1264 (1977).
G. F. Bol'shakov, V. S. Vatago, and F. B. Agrest, Ultraviolet Spectra of Heterocyclic Compounds [in Russian], Khimiya, Moscow (1969), p. 166.
A. Kalman, G. Argay, B. Ribar, and L. Toldy, Tetrahedron Lett., No. 48, 4241 (1977).
A. Zhunke, Nuclear Magnetic Resonance in Organic Chemistry [Russian translation], Mir, Moscow (1974), p. 37.
I. A. Litvinov, Yu. T. Struchkov, N. N. Bystrykh, Yu. P. Kitaev, and B. I. Buzykin, Khim. Geterotsikl. Soedin., No. 7, 977 (1982).
B. I. Buzykin, N. N. Bystrykh, A. P. Stolyarov, S. A. Flegontov, and Yu. P. Kitaev, Khim. Geterotsikl. Soedin., No. 4, 530 (1978).
B. I. Buzykin, O. P. Stolyarov (Stoljarov), and N. N. Bystrykh, Tetrahedron Lett., 21, 209 (1980).
A. Gordon and R. Ford, The Chemist's Companion, Wiley (1973).
Y. H. M. Hill and J. H. Ehrlich, J. Org. Chem., 36, 3248 (1971).
W. Flitsch and H. Peters, Angew. Chem., 79, 149 (1967).
Author information
Authors and Affiliations
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 826–833, June, 1983.
Rights and permissions
About this article
Cite this article
Bystrykh, N.N., Buzykin, B.I., Stolyarov, A.P. et al. Spectra and structure of 1-aminophthalazines. Chem Heterocycl Compd 19, 666–673 (1983). https://doi.org/10.1007/BF00523083
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF00523083