The reaction of 7-phenyl-7H-pyrazolo[3,4-d][1,2,3]triazin-4-ol with thionyl chloride has been studied in the presence and absence of dimethyl formamide. It was found that heating the compound with thionyl chloride in the absence of dimethyl formamide gave 5-amino-1-phenyl-1H-pyrazole-4-carboxylic acid chloride and in its presence a mixture of 5-chloro-N-formyl-1-phenyl-1H-pyrazole-4-carboxamide, 5-chloro-1-phenyl-1H-pyrazole-4-carboxamide, and 4-chloro-6-(5-chloro-1-phenyl-1H-pyrazol-4-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine.
Similar content being viewed by others
References
M. D. Mashkovskii, Drugs [in Russian], Vol. 1, Novaya Volna, Moscow (2000), p. 159.
A. A. Bekhit, H. M. Ashour, Y. S. Abdel Ghany, Ael-D. Bekhit, and A. Baraka, Eur. J. Med. Chem., 43, 456 (2008).
A. Padmaja, T. Payani, G. D. Reddy, and V. Padmavathi, Eur. J. Med. Chem., 44, 4557 (2009).
R. V. Ragavan, V. Vijayakumar, and N. S. Kumari, Eur. J. Med. Chem., 45, 1173 (2010).
S. M. Riyadh, T. A. Farghaly, M. A. Abdallah, M. M. Abdalla, and M. R. Abd El-Aziz, Eur. J. Med. Chem., 45, 1042 (2010).
M. A. El-borai, H. F. Rizk, M. F. Abd-Aal, and I. Y. El-Deeb, Eur. J. Med. Chem., 48, 92 (2012).
I. Vujasinovic, A. Paravic-Radicevic, K. Mlinaric-Majerski, K. Brajsa, and B. Bertosa, Bioorg. Med. Chem., 20, 2101 (2012).
X.-D. Yang, J. Chem. Res., 489 (2008).
B. M. Khutova, S. V. Klyuchko, A. O. Gurenko, A. N. Vasilenko, A. G. Balya, E. B. Rusanov, and V. S. Brovarets, Khim. Geterotsikl. Soedin., 1344 (2012). [Chem. Heterocycl. Compd., 48, 1251 (2012)].
N. P. Peet, J. Heterocycl. Chem., 23, 193 (1986).
R. D. Youssefyeh, R. E. Brown, J. Wilson, U. Shah, H. Jones, B. Loev, A. Khandwala, M. J. Leibowitz, and P. Sonnino-Goldman, J. Med. Chem., 27, 1639 (1984).
V. S. Mokrushin, V. I. Ofitserov, T. V. Rapakova, A. G. Tsaur, and Z. V. Pushkareva, Khim. Geterotsikl. Soedin., 556 (1976). [Chem. Heterocycl. Compd., 12, 465 (1976)].
V. S. Mokrushin, T. A. Pospelova, and Yu. M. Shafran, Khim. Geterotsikl. Soedin., 1548 (1983). [Chem. Heterocycl. Compd., 19, 1231 (1983)].
G. Ege and H. Franz, J. Heterocycl. Chem., 19, 1267 (1982).
P. Schmidt and J. Druey, Helv. Chim. Acta, 41, 306 (1958).
K. He, H. Lv, J. Wang, G. Qui, and X. Hu, J. Heterocycl. Chem., 45, 365 (2008).
G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 987-994, June, 2013.
Rights and permissions
About this article
Cite this article
Khutova, B.M., Klyuchko, S.V., Gurenko, A.O. et al. Reaction of 7-phenyl-7H-pyrazolo-[3,4-d][1,2,3]triazin-4-ol with thionyl chloride. Chem Heterocycl Comp 49, 922–929 (2013). https://doi.org/10.1007/s10593-013-1327-9
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-013-1327-9