Abstract
4-Amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-trazole-3-thione is formed from the reaction of 4,6-diphenylpyrimidinecarboxylic acid or its ethyl ester with thiocarbonyl hydrazide. Alkylation of the product leads to S-alkyl derivaties or 6-substituted 3-(4,6-diphenyl-2-pyriimidinyl)-7H-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazine. Acetylation of 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-thione gave under different conditions monoacetyl-, diacetyl, and triacetyl derivatives at the amino group and the N(2) atom, whereas benzoylation gave a benzoyl group at the amino group and 3-(4,6-diphenyl-2-pyrimidinyl)-6-phenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole.
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References
N. F. Eweiss, A. A. Bahajaj, and E. A. Elsherbini, J. Heterocycl. Chem., 23, 1451 (1986).
N. F. Eweiss and A. A. Bahajaj, J. Heterocycl. Chem., 24, 1173 (1987).
A. A. El-Barbary, M. Fahmy, M. El-Badawi, K. El-Brembaly, and N. R. El-Brollosi, Rev. Roum. Chim., 36, 619 (1991).
A. H. El-Masry, H. H. Fahmy, and S. H. Ali Abdelwahed, Molecules, 5, 1429 (2000).
K. Colonceska-Ragenovic, V. Dimova, V. Kakurinov, D. G. Molnar, and A. Buzarovska, Molecules, 6, 815 (2001).
N. Dembiras, A. Dembiras, S. A. Karaouglu, and E. Celik, ARKIVOC, 75 (2005).
A. R. Prasad, T. Ramalingam, A. B. Rao, P. V. Diwan, and P. B. Sattur, Indian. J. Chem., 25B, 566 (1986); Chem. Abstr, 106, 84500 (1987).
G. Mazzone, F. Bonina, A. M. Panico, M. Amico-Roxas, A. Caruso, G. Blandino, and A. Vanella, Farmaco, Ed. Sci., 42, 525 (1987); Chem. Abstr., 107, 168246 (1987).
A. R. Prasad, A. N. Rao, T. Ramalingam, and P. B. Sattur, Indian Drugs, 25, 301 (1988); Chem. Abstr., 109, 104366 (1988).
G. Mekuskiené, P. Gaidelis, and P. Vainilavicius, Pharmazie, 53, 94 (1998).
G. Mekuskiené, S. Tumkevicius, and P. Vainilavicius, J. Chem. Research (S), 213 (2002).
G. Mekuskiené, M. M. Burbuliene, V. Jakubkiene, E. Udrenaite, P. Gaidelis, and P. Vainilavièius, Khim. Geterotsikl. Soedin., 1548 (2003). [Chem. Heterocycl. Comp., 39, 1364 (2003)].
L. F. Audriet, E. S. Scott, and P. S. Kippur, J. Org. Chem., 19, 733 (1953).
V. Mamaev and E. A. Gracheva, Khim. Geterotsikl. Soedin., 1086 (1969). [Chem. Heterocycl. Comp., 5, 823 (1969)].
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, 1088–1094, July, 2007.
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Mekuškiene, G., Vainilavičius, P. Synthesis of 4-amino-5-(4,6-diphenyl-2-pyrimidinyl)-3,4-dihydro-2H-1,2,4-triazole-3-thione and its reactions with C-electrophiles. Chem Heterocycl Compd 43, 919–925 (2007). https://doi.org/10.1007/s10593-007-0145-3
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DOI: https://doi.org/10.1007/s10593-007-0145-3