Source: http://ophcj.nuph.edu.ua/article/view/ophcj.15.846
Timestamp: 2019-04-24 04:57:55+00:00

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It has been shown that the ternary condensation of oxaloacetic ester (diethyl 2-oxosuccinate), aromatic aldehydes and 3-amino-1,2,4-triazole or 5-aminotetrazole in dimethylformamide results in formation of the corresponding diethyl 7-aryl-4,7-dihydroazolo[1,5-a]pyrimidin-5,6-dicarboxylates. By 1H NMR spectroscopy (according to the data of the chemical shifts of C(2)H-protons for the corresponding N(4)H- and N(4)-methylderivatives of 7-phenyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-5,6-dicarboxylate) it has been found that alkylation of 4,7-dihydro[1,2,4]azolo[1,5-a]pyrimidin-5,6-dicarboxylates in the acetonitrile–saturated water alkali system leads selectively to formation of N(4)-alkyl derivatives. Both the starting compounds obtained and their N(4)-methylsubstituted analogues together with relative diethyl 4-aryl-3,4-dihydropyrimidin-2(1H)-on-5,6-dicarboxylates, 6-unsubstituted 4-aryl-3,4-dihydropyrimidin-2(1H)-on-5-dicarboxylates and the derivatives of 6-COR-7-aryl-4,7-dihydro[1,2,4] triazolo[1,5-a]pyrimidines are the promising objects for studying benzyl C(7)-functionalization of 4,7-dihydroazolo 1,5-a]pyrimidines, as well as of reactions associated with the presence of double C=C-bonds activated by two electron withdrawing groups. Obtaining of the key N(4)H- and N(4)Me-derivatives of 7-phenyl-4,7-dihydro[1,2,4] triazolo- and tetrazolo[1,5-a]pyrimidin-5,6-dicarboxylates also opens the way to the research of biological properties of the compounds of this class. It is noteworthy that being a three-component one the reaction studied, without any doubts, are appropriate for the synthesis of the derivatives of 7-aryl-4,7-dihydro[1,2,4]triazolo- and tetrazolo[1,5-a]pyrimidines containing two electron withdrawing substituents in positions 5 and 6.
Kolosov M. A., Al-Ogaili M. J. K., Orlov V. D. Bulletin of V.N.Karazin Kharkiv National University, 2012, No.1026, chem. ser., 21 (44), pp.108-111.
Kolosov M. A., Al-Ogaili M. J. K., Parkhomenko V. S., Orlov V. D. Chem. Heterocycl. Comp., 2013, Vol. 49, pp.1484-1489 [Хим. гетероцикл. соед., 2013, 49, 1599-1605]. doi: 10.1007/s10593-014-1399-1.
Fedorova O. V., Zhidovinova M. S., Rusinov G. L., Ovchinnikova I. G. Russ. Chem. Bull., 2003, Vol. 52, pp.1768-1769 [Изв. АН, сер. хим., 2003, 52, 1677- 1678]. doi: 10.1023/A:1026052603951.
Kumari K., Raghuvanshi D., Singh K. Org. Prep. Proced. Int., 2012, Vol. 44, pp.460-466. doi: 10.1080/00304948.2012.715062.
Ryabukhin S. V., Plaskon A. S., Boron S. Yu., Volochnyuk D. M., Tolmachev A. A. Mol. Divers, 2011, Vol. 15, pp.189-195. doi: 10.1007/s11030-010-9253-6.
Shaabani A., Rahmati, A., Rezayan A. H., Darvishi M., Badri Z., Sarvari A. QSAR Comb. Sci., 2007, Vol. 26, pp.973-979. doi: 10.1002/qsar.200620024.
Lipson V. V., Desenko S. M., Borodina V. V., Shirobokova M. G., Musatov V. I. Russ. J. Org. Chem., 2005, Vol. 41, pp.114-119 [Журн. орг. хим., 2005, 115- 120]. doi: 10.1007/s11178-005-0131-0.
Kolosov M. A., Kulyk O. G., Chepeleva L. V., Orlov V. D. Bulletin of V.N.Karazin Kharkiv National University, 2013, 1085, chem. ser., 22 (45), pp.39-44.
Folkers K., Harwood H. J., Johnson T. B. J. Am. Chem. Soc., 1932, Vol. 54, pp.3751-3758. doi: 10.1021/ja01348a040.
Kolosov M. A., Orlov V. D., Vashchenko V. V., Shishkina S. V., Shishkin O. V. Collect. Czech. Chem. Commun., 2007, Vol. 72, pp.1219-1228. doi: 10.1135/ cccc20071219.
Ryabukhin S. V., Plaskon A. S., Ostapchuk E. N., Volochnyuk D. M., Tolmachev A. A., Synthesis, 2007, Vol. 3, pp.417-427. doi: 10.1055/s-2007-965881.
Atwal K. S., O’Reilly B. C., Gougoutas J. Z., Malley M. F. Heterocycles, 1987, Vol. 26, pp.1189-1192. doi: 10.3987/R-1987-05-1189.
Atwal K. S., Swanson B. N., Unger S. E., Floyd D. M., Moreland S., Hedberg A., O’Reilly B. C. J. Med. Chem., 1991.,Vol 34, pp.806-811. doi: 10.1021/ jm00106a048.
Atwal K. S., Rovnyak G. C., Schwartz J., Moreland S., Hedberg A., Gougoutas J. Z., Malley M. F., Floyd D. M. J. Med. Chem., 1990, Vol. 33, pp.1510-1515. doi: 10.1021/jm00167a035.
Pryanishnikov N. D. Practical works in organic chemistry. Moscow, GNTIHL, 1956, 244 p. (in Russian).
Organicum: v 2 t. Per. s nem. 4-e ed. – Organic practical works. Moscow, Mir, 2008. – Т. 2. – 488 p. (in Russian).

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