[1,2,4]Triazolo[1,5-a]pyrimidines are very interesting and trend class of fused heterocycles due to their valuable biological properties. Some [1,2,4]-triazolo[1,5-a]pyrimidines possess herbicidal activity,1 also they can act as antifungal,2 antitubercular,3 and antibacterial4 agents. Polycyclic systems containing [1,2,4]triazolo[1,5-a]-pyrimidine moiety are reported as antitumor,5 as corticotropin-releasing factor 1 receptor antagonists6 or calcium channel modulators;7 they can be used for treatment of Alzheimer's disease8 and insomnia.9 Complexes of triazolo-pyrimidines with Pt and Ru are highly active against parasites10 and can also be used in treating cancer.11
The synthetic ways for the preparation of [1,2,4]triazolo[1,5-a]-pyrimidines can be divided into two main groups: annulation of pyrimidine moiety to triazole ring and annulation of triazole fragment to pyrimidine ring. The Dimroth rearrangement of [1,2,4]triazolo[4,3-a]pyrimidines can also be used for the synthesis of [1,2,4]triazolo[1,5-a]pyrimidines. In this review article we have focused on synthetic approaches for the creation of [1,2,4]triazolo[1,5-a]pyrimidine system.
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(a) Tang, W.; Shi, D.-Q. J. Heterocycl. Chem. 2010, 47, 162. (b) Jiang, L.; Chen, C.; Zhou, Y.; Chen, Q.; Yang, G. Chin. J. Org. Chem. 2009, 29(9), 1392.
(a) Xiong, Q.; Lin, X.; Liu, J.; Bi, L.; Bao, X. Chin. J. Org. Chem. 2012, 32, 1255. (b) Chen, Q.; Zhu, X.-L.; Jiang, L.-L.; Liu, Z.-M.; Yang, G.-F. Eur. J. Med. Chem. 2008, 43, 595.
(a) Bhatt, J. D.; Chudasama, C. J.; Patel, K. D. Bioorg. Med. Chem. 2015, 23, 7711. (b) Abdel-Rahman, H. M.; El-Koussi, N. A.; Hassan, H. Y. Arch. Pharm. Chem. Life Sci. 2009, 342, 94.
Wang, H.; Lee, M.; Peng, Z.; Blázquez, B.; Lastochkin, E.; Kumarasiri, M.; Bouley, R.; Chang, M.; Mobashery, S. J. Med. Chem. 2015, 58, 4194.
(a) Zhao, X.-L.; Zhao, Y.-F.; Guo, S.-C.; Song, H.-S.; Wang, D.; Gong, P. Molecules 2007, 12, 1136. (b) Hassan, G. S.; El-Sherbeny, M. A.; El-Ashmawy, M. B.; Bayomi, S. M.; Maarouf, A. R.; Badria, F. A. Arabian J. Chem. 2013. DOI: 10.1016/j.arabjc.2013.04.002.
Saito, T.; Obitsu, T.; Minamoto, C.; Sugiura, T.; Matsumura, N.; Ueno, S.; Kishi, A.; Katsumata, S.; Nakai, H.; Toda, M. Bioorg. Med. Chem. 2011, 19, 5955.
7. Hougaard, C.; Hammami, S.; Eriksen, B. L.; Sorensen, U. S.; Jensen, M. L.; Strobak, D.; Christophersen, P. Mol. Pharmacol. 2012, 81(2), 210.
Uryu, S.; Tokuhiro, S.; Murasugi, T.; Oda, T. Brain Research 2002, 946, 298.
Mustazza, C.; Del Giudice, M. R.; Borioni, A.; Gatta, F. J. Heterocycl. Chem. 2001, 38, 1119.
Salas, J. M.; Quiros, M.; Haj, M. A.; Magfin, R.; Marin, C.; Sfinchez-Moreno, M.; Faure, R. Met.-Based Drugs 2001, 8(3), 119.
Velders, A. H.; Bergamo, A.; Alessio, E.; Zangrando, E.; Haasnoot, J. G.; Casarsa, C.; Cocchietto, M.; Zorzet, S.; Sava, G. J. Med. Chem. 2004, 47, 1110.
(a) Pattan, Sh.; Hole, M.; Pattan, J.; Dengale, S.; Shinde, H., Muluk, R.; Nirmal, S., Jadhav, R. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2012, 51B, 774. (b) Bartels, B.; Bolas, C. G.; Cueni, P.; Fantasia, S.; Gaeng, N.; Trita A. S. J. Org. Chem. 2015, 80, 1249. (c) Song, L.; Tian, X.; Lv, Z.; Li, E.; Wu, J.; Liu, Y.; Yu, W.; Chang J. J. Org. Chem. 2015, 80, 7219.
Kishida, M.; Natsume, F.; Kawaguchi, Sh. Jpn. Kokai Tokkyo Koho 2004, 107228.
(a) Astakhov, A. V.; Chernyshev, V. M. Chem. Heterocycl. Compd. 2012, 48, 1417. [Khim. Geterotsikl. Soedin. 2012, 1519.] (b) Luo, Y.; Zhang, S.; Liu, Z.-J.; Chen, W.; Fu, J.; Zeng, Q.-F.; Zhu, H.-L. Eur. J. Med. Chem. 2013, 64, 54.
(a) Britsun, V. N.; Borisevich, A. N.; Samoilenko, L. S.; Chernega, A. N.; Lozinskii, M. O. Russ. J. Org. Chem. 2006, 42, 1516. (b) Britsun, V. N. Russ. J. Org. Chem. 2008, 44, 1528. (c) Zhai, X.; Zhao, Y.-F.; Liu, Y.-J. Zhang, Y.; Xun, F.-Q.; Liu, J.; Gong, P. Chem. Pharm. Bull. 2008, 56, 941.
(a) Chebanov, V. A.; Muravyova, E. A.; Desenko, S. M. Musatov, V. I.; Knyazeva, I. V.; Shishkina, S. V.; Shishkin, O. V.; Kappe, C. O. J. Comb. Chem. 2006, 8, 427. (b) Sedash, Yu. V.; Gorobets, N. Yu.; Chebanov, V. A.; Konovalova, I. S.; Shishkin, O. V.; Desenko, S. M. RSC Adv. 2012, 2, 6719. (c) Liu, J.; Lei, M.; Hu, L. Green Chem. 2012, 14, 840.
El-Gendy, M. M. A., Shaaban, M.; Shaaban, Kh. A.; El-Bondkly, A. M.; Laatsch, H. J. Antibiot. 2008, 61, 149.
(a) Battaglia, U.; Moody, C. J. J. Nat. Prod. 2010, 73, 1938. (b) Tee, E. H. L.; Karoli, T.; Ramu, S.; Huang, J. X.; Butler, M. S. Cooper, M. A. J. Nat. Prod. 2010, 73, 1940.
(a) Cernuchova, P.; Vo-Thanh, G.; Milata, V.; Loupy, A.; Jantova, S.; Theiszova, M. Tetrahedron 2005, 61, 5379. (b) Pryadeina, M. V.; Burgart, Y. V.; Saloutin, V. I.; Chupakhin, O. N. Mendeleev Commun. 2008, 18, 276. (c) Scapin, E.; Buriol, L.; München, T. S.; Frizzo, C. P.; Martins, M. A. P. In 15th Brazilian Meeting on Organic Synthesis – 15th BMOS, November 10–13, 2013. (d) Frizzo C. P., Scapin E., Marzari M. R. B., München T. S., Zanatta N., Bonacorso H. G., Buriol L., Martins M. A. P. Ultrason. Sonochemistry 2014, 21, 958. (e) Ahmed S. A., Ahmed O. M., Abdelhamid A. O. Eur. J. Chem. 2014, 5, 334. (f) Luo Y., Zhang Sh., Liu Zh.-J., Chen W., Fu J., Zeng Q.-F., Zhu H.-L. Eur. J. Med. Chem. 2013, 64, 54.
(a) Zhang, N.; Ayral-Kaloustian, S.; Nguyen, T.; Afragola, J.; Hernandez, R.; Lucas, J.; Gibbons, J.; Beyer, C. J. Med. Chem. 2007, 50, 319. (b) Chen, C.-N.; Lv, L.-L.; Ji, F.-Q.; Chen, Q.; Xu, H.; Niu, C.-W.; Xi, Z.; Yang, G.-F. Bioorg. Med. Chem. 2009, 17, 3011. (c) Huang, B.; Li, C.; Chen, W.; Liu, T.; Yu, M.; Fu, L.; Sun, Y.; Liu, H.; De Clercq, E.; Pannecouque, C.; Balzarini, J.; Zhan, P.; Liu, X. Eur. J. Med. Chem. 2015, 92, 754.
(a) Fizer, M. M.; Slivka, M. V.; Lendel, V. G. Chem. Heterocycl. Compd. 2013, 49, 1243. [Khim. Geterotsikl. Soedin. 2013, 1331.] (b) Fizer, M.; Slivka, M.; Rusanov, E.; Turov, A.; Lendel, V. J. Heterocycl. Chem. 2015, 52, 949.
Salgado, A.; Varela, C.; Collazo, A. M. G.; Garcia, F.; Pevarello, P.; Alkorta, I.; Elguero, J. J. Mol. Struct. 2011, 987, 13.
Vas'kevich, R. I.; Savitskii, P. V.; Zborovskii, Yu. L.; Staninets, V. I.; Rusanov, E. B.; Chernega, A. N. Russ. J. Org. Chem. 2006, 42, 1403.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(3), 155–157
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Fizer, M., Slivka, M. Synthesis of [1,2,4]triazolo[1,5-a]pyrimidine (microreview). Chem Heterocycl Comp 52, 155–157 (2016). https://doi.org/10.1007/s10593-016-1851-5
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DOI: https://doi.org/10.1007/s10593-016-1851-5