A method has been developed for obtaining thioamides of 5-amino-2-aryl-2H-1,2,3-triazole-4-carboxylic acid. Their heterocyclization reactions with bifunctional reagents has been studied. New heterocyclic polycyclic ensembles have been synthesized containing a 1,2,3-triazole fragment, a thiazole, and a residue of the natural alkaloid cytisine.
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N. P. Belskaya, M. A. Demina, S. G. Sapognikova, Z.-J. Fan, H.-Ke Zhang, W. Dehaen, and V. A. Bakulev, ARKIVOC, (xvi), 9 (2008).
T. S. Jagodzinski, Chem. Rev., 103, 197 (2003).
H. Takahata and T. Yamazaki, Heterocycles, 27, 1953 (1988).
E. Abdel-latif, and S. Bondok, Heteroatom. Chem., 17, 299 (2006).
R. N. Hurd and G. De LaMater, Chem. Rev., 61, 45 (1961).
K. A. Petrov and L. N. Andreev, Usp. Khim., 38, 41 (1969).
C. J. J. Goddart, J. Heterocycl. Chem., 28, 1607 (1991).
I. Yavari, S. Z. Sayeed-Alangi, R. Hajinasiri, and H. Sajjadi-Ghotbabadi, Monatsh. Chem., 140, 209 (2009).
A. Darehkordi, K. Saidi, and M. R. Islami, ARKIVOC, (i), 180 (2007).
N. A. Danilkina, L. E. Mikhailov, and B. A. Ivin, Russ. J. Org. Chem., 42, 783 (2006).
R. M. Acheson and J. D. Wallis, J. Chem. Soc., Perkin Trans. 1, 415 (1981).
O. V. Solod, K. N. Zelenin, and V. V. Pinson, Khim. Geterotsikl. Soedin., 3 (1996). [Chem. Heterocycl. Comp., 32, 1 (1996)].
G. M. Sheldrick, SHELXS97. Program for the Solution of Crystal Structures, Göttingen Univ., Göttingen (1997).
G. M. Sheldrick, SHELXL97. Program for the Refinement of Crystal Structures, Univ. of Göttingen, Göttingen (1997).
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Dedicated to Academician of the Russian Academy of Sciences O. N. Chupakhin on his 75th jubilee.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1061–1071, July, 2009.
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Belskaya, N.P., Sapozhnikova, S.G., Bakulev, V.A. et al. Synthesis and reactions of thioamides of 5-amino-2-aryl-2H-1,2,3-triazole-4-carboxylic acid. Chem Heterocycl Comp 45, 844–852 (2009). https://doi.org/10.1007/s10593-009-0348-x
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DOI: https://doi.org/10.1007/s10593-009-0348-x