Progress in the Synthesis of 1, 2, 4-Triazines by Tandem Cyclization
- Corresponding author: Huang Fei, huangfei0208@yeah.net
Citation:
Li Mingrui, Ding Qifeng, Li Boyang, Yu Yang, Huang He, Huang Fei. Progress in the Synthesis of 1, 2, 4-Triazines by Tandem Cyclization[J]. Chinese Journal of Organic Chemistry,
;2019, 39(10): 2713-2725.
doi:
10.6023/cjoc201905036
(a) Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Chem. Rev. 2014, 114, 2942.
(b) Kelly, T. R.; Elliott, E. L.; Lebedev, R.; Pagalday, J. J. Am. Chem. Soc. 2006, 128, 5646.
(c) Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794.
(a) Patrizia, D.; Annamaria, M.; Paola, B.; Antonino, L.; Alessandra, M.; Anna, M. A.; Gaetano, D.; Girolamo, C. Bioorg. Med. Chem. 2007, 15, 343.
(b) Tomas, G.; Eva, R.; Petr, D.; Marian, H.; Vladimir, K. Monatsh. Chem. 2010, 141, 709.
(c) Jaiprakash, N. S.; Devanand, B. S. Bioorg. Med. Chem. Lett. 2010, 20, 742.
(d) Badran, M. M.; Ismail, M. A. H.; Abdu, N.; Abdel-Hakeem, M. Alexandria J. Pharm. Sci. 1999, 13, 101.
(e) Thiele, K.; Gordon, C. J. S.; Fischer, J.; Jahn, U. EP 28660, 1981.
(f) Messmer, A.; Batori, S.; Hajos, G.; Benko, P. US 4602018, 1986.
(g) Kelly, T. R.; Elliott, E. L.; Lebedev, R.; Pagalday, J. J. Am. Chem. Soc. 2006, 128, 5646.
Solaleh, K. T.; Niloufar, A.; Mohsen, A. Apoptosis 2010, 15, 738.
doi: 10.1007/s10495-010-0496-6
(a) Hay, M. P.; Hicks, K. O.; Pchalek, K.; Lee, H. H.; Blaser, A.; Pruijn, F. B.; Anderson, R. F.; Shinde, S. S.; Wilson, W. R.; Denny, W. A. J. Med. Chem. 2008, 51, 6853.
(b) Vaithianathan, S.; Raman, S.; Jiang, W. L.; Ting, T. Y.; Kane, M. A.; Polli, J. E. Mol. Pharmaceutics 2015, 12, 2436.
(c) Lojanapiwat, B.; Nimitvilai, S.; Bamroongya, M.; Jirajariyavej, S.; Tiradechavat, C.; Malithong, A.; Predanon, C.; Tanphaichitra, D.; Lertsupphakul, B. Infect. Drug Resist. 2019, 12, 173.
Suzuki, H.; Kawakami, T. Synthesis 1997, 855.
Baxter, M. G; Elphick, A. R.; Miller, A. A. US 4486354, 1984.
Zhang, P.; Wang, J. J.; Xiao, H.; Jiang, Y.; Jiang, X. M. CN 103539803, 2014.
(a) Dowling, M. S.; Jiao, W. H.; Hou, J.; Jiang, Y. C.; Gong, S. S. J. Org. Chem. 2018, 83, 4229.
(b) Rätz, R.; Schroeder, H. J. Org. Chem. 1958, 23, 1931.
(c) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1971, 12, 2315.
(d) Kozhevnikov, V. N.; Kozhevnikov, D. N.; Shabunina, O. V.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2005, 46, 1791.
(a) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247
(b) Dydio, P.; Key, H. M.; Hayashi, H. J. Am. Chem. Soc. 2017, 139, 1750.
(c) Timsina, Y. N.; Gupton, B. F.; Ellis, K. C. ACS Catal. 2018, 8, 5732.
(d) Wang, P.; Li, G. C.; Jain, P. J. Am. Chem. Soc. 2016, 138, 14092.
Liu, L.; Tan, C.; Fan, R.; Wang, Z. H.; Du, H. G.; Xu, K.; Tan, J. J. Org. Biomol. Chem. 2019, 17, 252.
doi: 10.1039/C8OB02826E
Walsh, P. J.; Deng, G. G.; Li, M. Y.; Yu, K. L.; Liu, C. X.; Liu, Z. F.; Duan, S. Z.; Chen, W.; Yang, X. D.; Zhang, H. B. Angew. Chem., Int. Ed. 2019, 58, 2826.
doi: 10.1002/anie.201812369
Wang, J. N.; Chen, S. Q.; Liu, Z. W. J. Org. Chem. 2019, 84, 1348.
doi: 10.1021/acs.joc.8b02820
Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 117, 2250.
doi: 10.1002/ange.200461496
Guo, H. C.; Liu, H. L.; Zhu, F. L.; Na, R.; Jiang, H.; Wu, Y.; Zhang, L.; Li, Z.; Yu, H.; Wang, B.; Xiao, Y.; Hu, X. P.; Wang, M. Angew. Chem., Int. Ed. 2013, 52, 12641.
doi: 10.1002/anie.201307317
Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784.
doi: 10.1039/c1cc10779h
Du, J.; Xu, X.; Li, Y.; Pan, L.; Liu, Q. Org. Lett. 2014, 16, 4004.
doi: 10.1021/ol501829k
Cheng, X.; Cao, X.; Xuan, J.; Xiao, W. J. Org. Lett. 2018, 20, 52.
doi: 10.1021/acs.orglett.7b03344
Chen, Z.; Ren, N.; Ma, X. X.; Nie, J.; Zhang, F. G.; Ma, J. A. ACS Catal. 2019, 9, 4600.
doi: 10.1021/acscatal.9b00846
Hong, D.; Lin, X. F.; Zhu, Y. X.; Lei, M.; Wang, Y. G. Org. Lett. 2009, 11, 5678.
doi: 10.1021/ol902376w
Shi, B.; Lewis, W.; Campbell, I. B.; Moody, C. J. Org. Lett. 2009, 11, 3686.
doi: 10.1021/ol901502u
Wu, W.; Wang, J.; Wang, Y.; Huang, Y.; Tan, Y.; Weng, Z. Q. Angew. Chem., Int. Ed. 2017, 56, 10476.
doi: 10.1002/anie.201705620
Lin, B.; Wu, W.; Weng, Z. Q Tetrahedron 2019, 75, 2843.
doi: 10.1016/j.tet.2019.04.005
Meng, J.; Wen, M.; Zhang, S.; Pan, P.; Yu, X.; Deng, W. P. J. Org. Chem. 2017, 82, 1676.
doi: 10.1021/acs.joc.6b02846
Tang, D.; Wang, J.; Wu, P.; Guo, X.; Li, J. H.; Yang, S.; Chen, B. H. RSC Adv. 2016, 6, 12514.
doi: 10.1039/C5RA26638F
Zhang, L.; Chen, J. J.; Liu, S. S.; Liang, Y. X.; Zhao, Y. L. Adv. Synth. Catal. 2018, 360, 2172.
doi: 10.1002/adsc.201800030
Bigot, A.; Blythe, J.; Pandya, C.; Wagner, T.; Loiseleur, O. Org. Lett. 2010, 13, 192.
Crespin, L.; Biancalana, L.; Morack, T.; Blakemore, D. C.; Ley, S. V. Org. Lett. 2017, 19, 1084.
doi: 10.1021/acs.orglett.7b00101
Karthikeyan, M. S.; Mahalinga, M.; Karegoundar, P.; Poojary, B.; Holla, B. S. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 3231.
doi: 10.1080/10426500902979917
Tamboli, R. S.; Giridhar, R.; Mande, H. M.; Shah, S. R.; Yadav, M. R. Synth. Commum. 2014, 44, 2192.
doi: 10.1080/00397911.2014.891040
Ghorbani-Vaghei, R.; Shahriari, A.; Salimi, Z.; Hajinazari, S. RSC Adv. 2015, 5, 3665.
doi: 10.1039/C4RA10892B
Savva, A. C.; Mirallai, S. I.; Zissimou, G. A.; Berezin, A. A.; Demetriades, M.; Kourtellaris, A.; Constantinides, C. P.; Nicolaides, C.; Trypiniotis, T, ; Koutentis, P. A. J. Org. Chem. 2017, 82, 7564.
doi: 10.1021/acs.joc.7b01297
Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; Jesús, M. Tetrahedron 2007, 63, 523.
doi: 10.1016/j.tet.2006.09.048
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