Progress in the Synthesis of 1,2,4-Triazines by Tandem Cyclization

doi:10.6023/cjoc201905036

Chinese Journal of Organic Chemistry ›› 2019, Vol. 39 ›› Issue (10): 2713-2725.DOI: 10.6023/cjoc201905036 Previous Articles Next Articles

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基于串联环化反应合成1,2,4-三嗪类化合物的研究进展

李明瑞^a, 丁奇峰^a, 李博洋^a, 于杨^c, 黄和^a^b, 黄菲^a^b^*()

^a 南京工业大学药学院南京 211816
^b 南京师范大学食品与制药工程学院南京 210023
^c 南京工业大学环境科学与工程学院南京 211816

收稿日期:2019-05-14 修回日期:2019-06-03 发布日期:2019-06-24
通讯作者: 黄菲 E-mail:huangfei0208@yeah.net
基金资助:
国家自然科学基金(21901124);江苏省高等学校自然科学研究面上项目(19KJB150032);中国博士后科学基金(2019M651809);江苏省先进生物制造创新中心(XTE1850);安徽省博士后科研活动经费(No. 2018B252)资助项目(2018B252)

Progress in the Synthesis of 1,2,4-Triazines by Tandem Cyclization

Li Mingrui^a, Ding Qifeng^a, Li Boyang^a, Yu Yang^c, Huang He^a^b, Huang Fei^a^b^*()

^a School of Pharmaceutical Sciences, Nanjing Tech University, Nanjing 211816
^b School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, Nanjing 210023
^c School of Environmental and Engineering, Nanjing Tech University, Nanjing 211816

Received:2019-05-14 Revised:2019-06-03 Published:2019-06-24
Contact: Huang Fei E-mail:huangfei0208@yeah.net
Supported by:
Project supported by the National Natural Science Foundation of China(21901124);The Jiangsu University Natural Science Research Program(19KJB150032);The China Postdoctoral Science Foundation(2019M651809);The Jiangsu Synergetic Innovation Center for Advanced Bio-Manufacture(XTE1850);The Postdoctoral Science Foundation of Anhui Province(2018B252)

1,2,4-Triazine compounds are an important class of nitrogen-containing heterocyclic compounds. They have wide applications in the fields of medicine, chemicals and materials. Therefore, green and highly efficient synthesis of 1,2,4-triazine compounds is increasingly attracting the attention of researchers. By tandem cyclization reaction, the post-treatment of intermediate is avoided, and the one-pot synthesis of triazine compounds is the most efficient and direct synthesis method, which conforms to the concept of green chemistry for its step and atomic economy. The formation of C—N bond based on tandem cyclization to give 1,2,4-triazine compounds is reviewed. The synthetic method, reaction mechanism and application of 1,2,4-triazine compounds are introduced under transition-metal and metal-free conditions in the past ten years. The prospects of synthesis of triazine rings are also discussed.

Key words: 1,2,4-triazine, tandem cyclization, C—N bond formation, transition-metal catalysis, metal-free catalysis

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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.

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Fig. & Tab. 25

Scheme 1. Derivatives synthesized via a 1,2,4-triazine ring

Figure 1. Pharmaceutically active molecule containing 1,2,4-triazine ring

Scheme 2. Synthetic method containing triazine ring skeleton drug

Scheme 3. Classical synthesis method of 1,2,4-triazine

Figure 2. Ferrocenyl P,N ligands

Scheme 4. Possible reaction mechanism between isocyanate and 1,3-azomethyleneimine catalyzed by copper salt

Scheme 5. Silver trifluoromethanesulfonate catalytic process

Scheme 6. In situ formation of triazine compounds

Scheme 7. Silver-catalyzed [3+3] dipolar cycloaddition reaction

Scheme 8. Mechanism experiment

Scheme 9. Possible reaction process

Scheme 10. Two possible reaction processes

Scheme 11. Copper(II) catalyzed N—H insertion synthesis of 1,2,4-triazine compounds

Scheme 12. Synthesis of 1,2,4-triazine by interrupting click chemistry

Scheme 13. Possible reaction mechanism

Scheme 14. Ruthenium catalyzed cyclization/oxidation

Scheme 15. Reaction process of Ruthenium-catalyzed C—H insertion and subsequent oxidation

Scheme 16. Possible reaction process between two substrates

Scheme 17. DBU-catalyzed [3+3] cyclization of imine with α-diazo ester compounds

Scheme 18. Possible reaction mechanism of DBU catalyzed tandem cyclization

Scheme 19. Acid-catalyzed synthesis of polysubstituted triazine compounds

Scheme 20. Lewis acid and base catalyzed ring opening/closing process of aziridine

Scheme 21. Small molecule coupling synthesis of 1,2,4-triazine

Scheme 22. Possible reaction process

Scheme 23. Aza-Wittig-mediated possible process of Blatter radical synthesis

References 34

[1]	(a) Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Chem. Rev. 2014, 114, 2942. doi: 10.1021/cr300122t
	(b) Kelly, T. R.; Elliott, E. L.; Lebedev, R.; Pagalday, J. J. Am. Chem. Soc. 2006, 128, 5646. doi: 10.1021/cr300122t
	(c) Blair, L. M.; Sperry, J. J. Nat. Prod. 2013, 76, 794. doi: 10.1021/cr300122t
[2]	(a) Egorov, I. N.; Tseitler, T. A.; Kovalev, I. S.; Slepukhin, P. A.; Rusinov, V. L.; Chupakhin, O. N. J. Org. Chem. 2012, 77, 6007. doi: 10.1021/jo300697v
	(b) Raw, S. A.; Taylor, R. J. K. J. Am. Chem. Soc. 2004, 126, 12260. doi: 10.1021/jo300697v
	(c) Sainz, Y. F.; Raw, S. A.; Taylor, R. J. K. J. Org. Chem. 2005, 70, 10086. doi: 10.1021/jo300697v
	(d) Ye, L.; Haddadin, M. J.; Lodewyk, M. W.; Ferreira, A. J.; Fettinger, J. C.; Tantillo, D. J.; Kurth, M. J. Org. Lett. 2010, 12, 164. doi: 10.1021/jo300697v
	(e) Lewis, F. W.; Harwood, L. M.; Hudson, M. J.; Geist, A.; Kozhevnikov, V. N.; Distler, P.; John, J. Chem. Sci. 2015, 6, 4812. doi: 10.1021/jo300697v
	(f) Kamber, D. N.; Liang, Y.; Blizzard, R. J.; Liu, F.; Mehl, R. A.; Houk, K. N.; Prescher, J. A. J. Am. Chem. Soc. 2015, 137, 8388. doi: 10.1021/jo300697v
	(g) Stanforth, S. P.; Tarbit, B.; Watson, M, D. Tetrahedron. 2004, 60, 8893. doi: 10.1021/jo300697v
	(h) Suleymanova, A. F.; Kozhevnikov, D. N.; Prokhorov, A. M. Tetrahedron Lett. 2012, 53, 5293. doi: 10.1021/jo300697v
	(i) Kopchuk, D. S.; Nikonov, I. L.; Khasanov, A. F.; Giri, K.; Santra, S.; Chupakhin, O. N. Org. Biomol Chem. 2018, 16, 5119. doi: 10.1021/jo300697v
	(j) Glinkerman, C. M.; Boger, D. L. J. Am. Chem. Soc. 2016, 138, 12408. doi: 10.1021/jo300697v
	(k) Boger, D. L.; Panek, J. S. J. Org. Chem. 1981, 46, 2179. doi: 10.1021/jo300697v
	(l) Zhang, C. L.; Li, Y. Z.; Li, J. Y.; Li, Y. L.; Gong, R. Q.; Wang, H. Y. Chin. J. Org. Chem.(in Chinese). 2018, 38, 2720. doi: 10.1021/jo300697v
	( 张成路, 李益政, 李静怡, 李奕嶙, 宫荣庆, 王华玉, 有机化学, 2018, 38, 2720.) doi: 10.1021/jo300697v
[3]	(a) Patrizia, D.; Annamaria, M.; Paola, B.; Antonino, L.; Alessandra, M.; Anna, M. A.; Gaetano, D.; Girolamo, C. Bioorg. Med. Chem. 2007, 15, 343. doi: 10.1016/j.bmc.2006.09.054
	(b) Tomas, G.; Eva, R.; Petr, D.; Marian, H.; Vladimir, K. Monatsh. Chem. 2010, 141, 709. doi: 10.1016/j.bmc.2006.09.054
	(c) Jaiprakash, N. S.; Devanand, B. S. Bioorg. Med. Chem. Lett. 2010, 20, 742. doi: 10.1016/j.bmc.2006.09.054
	(d) Badran, M. M.; Ismail, M. A. H.; Abdu, N.; Abdel-Hakeem, M. Alexandria J. Pharm. Sci. 1999, 20, 101. doi: 10.1016/j.bmc.2006.09.054
	(e) Thiele, K.; Gordon, C. J. S.; Fischer, J.; Jahn, U. EP 28660, 1981. doi: 10.1016/j.bmc.2006.09.054
	(f) Messmer, A.; Batori, S.; Hajos, G.; Benko, P. US 4602018, 1986. doi: 10.1016/j.bmc.2006.09.054
	(g) Kelly, T. R.; Elliott, E. L.; Lebedev, R.; Pagalday, J. J. Am. Chem. Soc. 2006, 128, 5646. doi: 10.1016/j.bmc.2006.09.054
[4]	Solaleh, K. T.; Niloufar, A.; Mohsen, A. Apoptosis 2010, 15, 738. doi: 10.1007/s10495-010-0496-6
[5]	(a) Moses, G. G.; Jeremy, P. O.; Elizabeth, B. B. Tetrahedron Lett. 2011, 52, 3345. doi: 10.1016/j.tetlet.2011.04.075
	(b) Xu, H. N.; Lou, J. Y.; Zhang, C.; Liu, H. M.; Liu, S. J.; Wen, Z. C.; Wang, Y.; Lin, H. Q.; Hu, C. Chin. J. New Drugs 2013, 22, 2692 (in Chinese). doi: 10.1016/j.tetlet.2011.04.075
	( 徐赫男, 娄晶莹, 张灿, 刘宏民, 刘斯婕, 温志昌, 王言, 林煌权, 胡春, 中国新药杂志, 2013, 22.) doi: 10.1016/j.tetlet.2011.04.075
[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. doi: 10.1021/jm800967h
	(b) Vaithianathan, S.; Raman, S.; Jiang, W. L.; Ting, T. Y.; Kane, M. A.; Polli, J. E. Mol. Pharmaceutics 2015, 12, 2436. doi: 10.1021/jm800967h
	(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. doi: 10.1021/jm800967h
[7]	Suzuki, H.; Kawakami, T . Synthesis 1997,855.
[8]	Baxter, M. G.; Elphick, A. R.; Miller, A. A . US 4486354, 1984.
[9]	Zhang, P.; Wang, J. J.; Xiao, H.; Jiang, Y.; Jiang, X. M . CN 103539803, 2014.
[10]	(a) Dowling, M. S.; Jiao, W. H.; Hou, J.; Jiang, Y. C.; Gong, S. S. J. Org. Chem. 2018, 83, 4229. doi: 10.1021/acs.joc.8b00254
	(b) Rätz, R.; Schroeder, H. J. Org. Chem. 1958, 23, 1931. doi: 10.1021/acs.joc.8b00254
	(c) Saraswathi, T. V.; Srinivasan, V. R. Tetrahedron Lett. 1971, 12, 2315. doi: 10.1021/acs.joc.8b00254
	(d) Kozhevnikov, V. N.; Kozhevnikov, D. N.; Shabunina, O. V.; Rusinov, V. L.; Chupakhin, O. N. Tetrahedron Lett. 2005, 46, 1791. doi: 10.1021/acs.joc.8b00254
[11]	(a) Park, Y.; Kim, Y.; Chang, S. Chem. Rev. 2017, 117, 9247. doi: 10.1021/acs.chemrev.6b00644
	(b) Dydio, P.; Key, H. M.; Hayashi, H. J. Am. Chem. Soc. 2017, 139, 1750. doi: 10.1021/acs.chemrev.6b00644
	(c) Timsina, Y. N.; Gupton, B. F.; Ellis, K. C. ACS Catal. 2018, 8, 5732. 14092. doi: 10.1021/acs.chemrev.6b00644
	(d) Wang, P.; Li, G. C.; Jain, P. J. Am. Chem. Soc. 2016, 138, 14092. doi: 10.1021/acs.chemrev.6b00644
[12]	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
[13]	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
[14]	Wang, J. N.; Chen, S. Q.; Liu, Z. W. J. Org. Chem. 2019, 84, 1348. doi: 10.1021/acs.joc.8b02820
[15]	Rodionov, V. O.; Fokin, V. V.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 117, 2250. doi: 10.1002/(ISSN)1521-3757
[16]	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
[17]	Adrio, J.; Carretero, J. C. Chem. Commun. 2011, 47, 6784. doi: 10.1039/c1cc10779h
[18]	Du, J.; Xu, X.; Li, Y.; Pan, L.; Liu, Q. Org. Lett. 2014, 16, 4004. doi: 10.1021/ol501829k
[19]	Cheng, X.; Cao, X.; Xuan, J.; Xiao, W. J. Org. Lett. 2018, 20, 52. doi: 10.1021/acs.orglett.7b03344
[20]	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
[21]	Hong, D.; Lin, X. F.; Zhu, Y. X.; Lei, M.; Wang, Y. G. Org. Lett. 2009, 11, 5678. doi: 10.1021/ol902376w
[22]	Shi, B.; Lewis, W.; Campbell, I. B.; Moody, C. J. Org. Lett. 2009, 11, 3686. doi: 10.1021/ol901502u
[23]	Wu, W.; Wang, J.; Wang, Y.; Huang, Y.; Tan, Y.; Weng, Z. Q. Angew. Chem., Int. Ed. 2017, 56, 10476. doi: 10.1002/anie.v56.35
[24]	Lin, B.; Wu, W.; Weng, Z. Q Tetrahedron. 2019, 75, 2843. doi: 10.1016/j.tet.2019.04.005
[25]	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
[26]	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
[27]	Zhang, L.; Chen, J. J.; Liu, S. S.; Liang, Y. X.; Zhao, Y. L . Adv. Synth. Catal. 2018, 360, 2172. doi: 10.1002/adsc.v360.11
[28]	Bigot, A.; Blythe, J.; Pandya, C.; Wagner, T.; Loiseleur, O. Org. Lett. 2010, 13, 192. doi: 10.1021/ol102454e
[29]	Crespin, L.; Biancalana, L.; Morack, T.; Blakemore, D. C.; Ley, S. V. Org. Lett. 2017, 19, 1084. doi: 10.1021/acs.orglett.7b00101
[30]	Karthikeyan, M. S.; Mahalinga, M.; Karegoundar, P.; Poojary, B.; Holla, B. S. Phosphorus, Sulfur Silicon Relat. Elem. 2009, 184, 3231.
[31]	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
[32]	Ghorbani-Vaghei, R.; Shahriari, A.; Salimi, Z.; Hajinazari, S. RSC Adv. 2015, 5, 3665. doi: 10.1039/C4RA10892B
[33]	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.
[34]	Palacios, F.; Alonso, C.; Aparicio, D.; Rubiales, G.; Jesús, M. Tetrahedron 2007, 63, 523. doi: 10.1016/j.tet.2006.09.048

基于串联环化反应合成1,2,4-三嗪类化合物的研究进展

Progress in the Synthesis of 1,2,4-Triazines by Tandem Cyclization

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Fig. & Tab. 25

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