Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block

doi:10.6023/cjoc202208020

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (2): 436-454.DOI: 10.6023/cjoc202208020 Previous Articles Next Articles

以氨基氰为原料合成含氮化合物的研究进展

吴江龙^†, 王中杰^†, 王晨宇, 王彦, 李红俊, 罗辉, 李昊, 王富强^*(), 李典军^*(), 杨金会^*()

宁夏大学化学化工学院/省部共建煤炭高效利用与绿色化工国家重点实验室银川 750021

收稿日期:2022-08-16 修回日期:2022-09-18 发布日期:2022-10-31
作者简介:
†共同第一作者
基金资助:
部委级自然科学其他项目(2019NXZD1); 宁夏自治区科技攻关(支撑)计划(2021BEG02001); 宁夏自治区科技攻关(支撑)计划(2021BEE03003); 及宁夏自治区重点研发计划(2022BDE03009)

Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block

Jianglong Wu^†, Zhongjie Wang^†, Chenyu Wang, Yan Wang, Hongjun Li, Hui Luo, Hao Li, Fuqiang Wang(), Dianjun Li(), Jinhui Yang()

College of Chemistry and Chemical Engineering/State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, Ningxia University, Yinchuan 750021

Received:2022-08-16 Revised:2022-09-18 Published:2022-10-31
Contact: *E-mail: nxlidj@126.com;6960463@qq.com;yang_jh@nxu.edu.cn
About author:
†(These authors contributed equally to this work).
Supported by:
Ministry-Level Natural Science Other Projects(2019NXZD1); Scientific and Technological Research (Support) Project of Ningxia(2021BEG02001); Scientific and Technological Research (Support) Project of Ningxia(2021BEE03003); Key Research and Development Project of Ningxia(2022BDE03009)

Nitrogen-containing compounds are widely found in many natural products and have a wide range of pharmaco- logical and physiological activities. Furthermore, they have comprehensive applications in medicine and pesticide fields, industry and multi-functional materials. Great advances in the synthesis of these compounds have been sprung up, a diversity of synthetic methods of them via cyanamide (NH₂-CN) as raw material were exploited in recent years. The research progress on the synthesis of nitrogen-containing compounds through cyanamide as a building block is introduced comprehensively. Moreover, their characteristics, rules, advantages and disadvantages are summarized and discussed for the development of new synthetic methodologies and reactions of nitrogen-containing compounds.

Key words: cyanamide, natural origin, nitrogen-containing compound, pharmaceutical

Cite this article

Jianglong Wu, Zhongjie Wang, Chenyu Wang, Yan Wang, Hongjun Li, Hui Luo, Hao Li, Fuqiang Wang, Dianjun Li, Jinhui Yang. Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block[J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 436-454.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 28

Figure 1. A variety of nitrogen-containing heterocyclic drug molecules with biological activity and medicinal value

Scheme 1. Desired transformation to guanidine intermediate 13

Scheme 2. Pd-catalyzed carbonylative one-pot synthesis of N-acylguanidines

Scheme 3. Iodinane and metal-free synthesis of N-cyano sulfilimines

Scheme 4. Cyanoimidation of aldehydes using cyanamide and NBS

Scheme 5. Synthesis of N-(1H)-tetrazole sulfoximines

Scheme 6. Route to synthesize pinacidil using cyanamide as block

Scheme 7. Copper-catalyzed synthesis of benzimidazo[2,1-b]quinazolin-12(6H)-ones from cyanamide

Scheme 8. Copper-catalyzed reaction of 2-bromo-N-(2-bromophenyl)benzamide and cyanamide for the synthesis of benzimidazo- [2,1-b]quinazolin-12(6H)-ones

Scheme 9. Synthesis of aminonicotinonitriles through base-catalyzed with cyanamide

Scheme 10. Synthesis of amino oxazoline from cyanamide

Scheme 11. Synthesis of polyfunctionalized 2-aminoimidazoles via vinyl azides and cyanamide

Scheme 12. Strategy for 2-aminoimidazoles via ring opening of α-nitro epoxides and and cyanamide

Figure 2. Drug molecules containing purine building block

Scheme 13. A one-pot, three-component reaction of cyanamides, 5-aminopyrazole-4-carbonitriles and triethyl or thoformate for the synthesis of 4-aminopyrazolotriazine nitrile compounds

Figure 3. Drug molecules containing pyrimidine building block

Scheme 14. Acid catalytic microwave-assisted synthesis of pyrazolopyrimidines from cyanamide

Scheme 15. Proposed reaction mechanism of synthesis of pyrazolopyrimidine from cyanamide

Scheme 16. Synthesis of substituted pyrimidines from nitriles

Scheme 17. Route to synthesize antifungal drug using cyanamide as block

Scheme 18. A one-pot, reaction of cyanamides and dithioesters for the synthesis of 2-(hetero)aryl thiazoles compounds

Scheme 19. Synthesis of benzotriazine from nitroaniline and cyanamine

Scheme 20. Synthesis of acridine derivatives from cyanogen

Scheme 21. A one-pot, three-component reaction of cyanamides, methyl ketones and arylamines for the synthesis of 2-amino-triazines

Scheme 22. Strategies for synthesizing nucleobase of rindesivir

Scheme 23. Diversity-oriented synthesis of 1,2 4-triazols, 1,3,4-thiadiazols, and 1,3,4-selenadiazoles from N-tosylhydrazones

Scheme 24. Synthesis of 1,2,4-triazole compounds from cyanamide and N-toluenesulfonyl hydrazone

Scheme 25. Synthesis of 3-trifluoromethyl-1,2,4-triazolines via tandem addition/cyclization of trifluoromethyl N-acylhydrazones with cyanamide

References 96

[1]	Romagnoli, R.; Baraldi, P. G.; Carrion, M. D. J. Med. Chem. 2009, 52, 5551. doi: 10.1021/jm9001692 pmid: 19663386
[2]	Abdelazeem, A. H.; Abdelatef, S. A.; El-Saadi, M. T. Eur. J. Pharm. Sci. 2014, 62,197.
[3]	Zhu, Y.; Loso, M. R.; Watson, G. B. J. Agric. Food Chem. 2011, 59, 2950. doi: 10.1021/jf102765x
[4]	Lainé, D.; Palovich, M.; McCleland, B. ACS Med. Chem. Lett. 2011, 2, 142. doi: 10.1021/ml100212k
[5]	Stafford, J. A.; Feldman, P. L. Annu. Rep. Med. Chem. 1996, 31,71.
[6]	David, H. D.; Samuel, W. G.; James, A. L. Tetrahedron Lett. 1997, 38, 3377. doi: 10.1016/S0040-4039(97)00653-9
[7]	Berlinck, R. G. S. Fortschr. Chem. Org. Naturst. 1995, 66,119.
[8]	Castagnolo, D.; Schenone, S.; Botta, M. Chem. Rev. 2011, 111, 5247. doi: 10.1021/cr100423x pmid: 21657224
[9]	Patrick, C. K.; Monica, F.; John, A. F. Tetrahedron Lett. 1998, 39, 2663.
[10]	Kamo, T.; Endo, M.; Sato, M. Phytochemistry 2008, 69, 1166. doi: 10.1016/j.phytochem.2007.11.004
[11]	Chen, X.; Orser, B. A.; MacDonald, J. F. Eur. J. Pharmacol. 2010, 648, 15. doi: 10.1016/j.ejphar.2010.09.005
[12]	Ojo, B.; Dunbar, P. G.; Durant, G. J. Bioorg. Med. Chem. 1996, 4, 1605. doi: 10.1016/0968-0896(96)00152-6
[13]	Cannon, C. P. Clin. Cardiol. 2003, 26, 358. doi: 10.1002/clc.4950260803
[14]	Kotthaus, J.; Steinmetzer, T.; van de Locht, A. J. Enzyme Inhib. Med. Chem. 2011, 26, 115. doi: 10.3109/14756361003733647
[15]	Sävmarker, J.; Rydfjord, J.; Gising, J.; Odell, L. R.; Larhed, M. Org. Lett. 2012, 14, 2394. doi: 10.1021/ol300813c
[16]	Rydfjord, J.; Svensson, F.; Trejos, A.; Sjçberg, J. R.; Skçld, C.; vmarker, J. S.; Odell, L. R.; Larhed, M. Chem. Small. 2013, 19, 13803.
[17]	Rydfjord, J.; Skillinghaug, B.; Brandt, P.; Odell, L. R.; Larhed, M. Org. Lett. 2017, 19, 4066. doi: 10.1021/acs.orglett.7b01836 pmid: 28741950
[18]	Klein, M.; Güthner, T.; Sans, J. Green Chem. 2021, 23, 3289-3294. doi: 10.1039/D1GC00700A
[19]	(a) Odo, K.; Sugino, K. J. Electrochem. Soc. 1957, 104, 160. doi: 10.1149/1.2428525
	(b) Ichikawa, E.; Odo, K. Denki Kagaku 1964, 32, 897.
[20]	Katritzky, A. R.; Khashab, N. M.; Bobrov, S. Helv. Chim. Acta 2005, 88, 1664. doi: 10.1002/hlca.200590131
[21]	Yong, Y. F.; Kowalski, J.; Lipton, M. J. Org. Chem. 1997, 62, 1540. doi: 10.1021/jo962196k
[22]	Andrews, D.; Finlay, M. R.; Green, C.; Jones, C.; Oza, V. WO 095159, 2006.
[23]	Bicking, J. B.; Mason, J. W.; Woltersdorf Jr, O. W. J. Med. Chem. 1965, 8, 638. doi: 10.1021/jm00329a017
[24]	Pacha, W.; Salzmann, R.; Scholtysik, G. Br. J. British. J. Pharmacol. 1975, 53, 513.
[25]	Åkerbladh, L.; Schembri, L S.; Larhed, M.; Odell, L. R. J. Org. Chem. 2017, 82, 12520. doi: 10.1021/acs.joc.7b02294 pmid: 29027801
[26]	Miller, A. J. Org. Chem. 1984, 49, 4072. doi: 10.1021/jo00195a043
[27]	Mancheno, O. G.; Bistri, O.; O.; Bolm, C. Org. Lett. 2007, 9, 3809. doi: 10.1021/ol7016577
[28]	(a) Serban, G. Molecules 2020, 25, 942. doi: 10.3390/molecules25040942
	(b) Gao, F.; Wang, T.; Xiao, J.; Huang, G. Eur. J. Med. Chem. 2019, 173, 274. doi: 10.1016/j.ejmech.2019.04.043
[29]	Yin, P.; Ma, W. B.; Chen, Y.; Huang, W. C.; Deng, Y.; He, L. Org. Lett. 2009, 5482.
[30]	(a) Hiskey, M.; Chavez, D. E.; Naud, D. L. Proc. Int. Pyrotech. Semin. 2000, 27, 3. pmid: 7031768
	(b) Singh, H.; Chawla, A. S.; Kapoor, V. K. Prog. Med. Chem. 1980, 17, 151. pmid: 7031768
[31]	Moderhack, D. J. Prakt. Chem. 1998, 340, 687. doi: 10.1002/prac.19983400802
[32]	García Mancheño, O.; Bolm, C. Org. Lett. 2007, 9, 2951. pmid: 17595098
[33]	For an example of guanidine synthesis with cyanamide and carbodiimide see: Mestres, R.; Palomo, C. Synthesis 1980, 755.
[34]	Baeten, M.; Maes, B. U. W. Adv. Synth. Catal. 2016, 358, 826. doi: 10.1002/adsc.201501146
[35]	Nordeman, P.; Chow, S. Y.; Odell, A. F. Org. Biomol. Chem. 2017, 15, 4875. doi: 10.1039/c7ob01064h pmid: 28537303
[36]	Ma, X. D.; Huang, W.; Yang, Y. Y. CN 112979555, 2021.
[37]	Lunn, W. H. W.; Harper, R. W.; Stone, R. L. J. Med. Chem. 1971, 14, 1069. pmid: 5115206
[38]	(a) Li, X.; Gan, B.; Xie, T. J. Chem. Res. 2016, 40, 178. doi: 10.3184/174751916X14558161990884
	(b) Hua, G.; Li, Y.; Fuller, A. Eur. J. Org. Chem. 2009, 2009, 1612. doi: 10.1002/ejoc.200900013
[39]	(a) Bird, C. W. Tetrahedron 1965, 21, 2179. doi: 10.1016/S0040-4020(01)98354-1 pmid: 17194113
	(b) Bird, C. W.; Kapilli, M. Tetrahedron 1987, 43, 4621. doi: 10.1016/S0040-4020(01)86904-0 pmid: 17194113
	(c) Fadda, A. A.; Refat, H. M.; Zaki, M. E.; Monir, A. E. Synth. Commun. 2001, 31, 3537. doi: 10.1081/SCC-100106216 pmid: 17194113
	(d) Carpenter, R. D.; Lam, K. S.; Kurth, M. J. J. Org. Chem. 2007, 72, 284. pmid: 17194113
[40]	Yang, D. S.; Wang, Y. Y.; Yang, H. J.; Liu, T.; Fu, H. Adv. Synth. Catal. 2012, 354, 477. doi: 10.1002/adsc.201100580
[41]	Lou, Z. B.; Wu, X. D.; Yang, H. J.; Zhu, C. J.; Fu, H. Adv. Synth. Catal. 2015, 357, 3961. doi: 10.1002/adsc.201500577
[42]	Mishra, N.; Singh, A. S.; Agrahari, A. K.; Singh, S. K.; Singh, M.; Tiwari, V. K. ACS Comb. Sci. 2019, 21, 389. doi: 10.1021/acscombsci.9b00004 pmid: 30943366
[43]	Farhanullah; Agarwal, N.; Goel A.; Ram, V. J. J. Org. Chem. 2003, 68, 2983. pmid: 12662083
[44]	Zhang, L.; Peng, X. M.; Damu, G. L. V. Med. Res. Rev. 2014, 34, 340. doi: 10.1002/med.21290 pmid: 23740514
[45]	Anastasi, C.; Crowe, M. A.; Powner, M. W.; Sutherland, J. D. Angew. Chem., nt. Ed. 2006, 45, 6176.
[46]	Fahrenbach, A. C.; Giurgiu, C.; Tam, C. P.; Li, L.; Hongo, Y.; Aono, M.; Szostak, J. W. J. Am. Chem. Soc. 2017, 139, 8780. doi: 10.1021/jacs.7b01562 pmid: 28640999
[47]	Cohen, S. H.; Gerding, D. N.; Johnson, S. Infect. Control Hosp. Epidemiol. 2010, 31, 431. doi: 10.1086/651706
[48]	Malamas, M. S.; Erdei, J.; Gunawan, I. J. Med. Chem. 2010, 53, 1146. doi: 10.1021/jm901414e
[49]	Li, W. T.; Hwang, D. R.; Song, J. S. J. Med. Chem. 2010, 53, 2409. doi: 10.1021/jm901501s
[50]	Nishimura, T.; Kitajima, K. J. Org. Chem. 1979, 44, 818. doi: 10.1021/jo01319a034
[51]	Little, T. L.; Webber, S. E. J. Org. Chem. 1994, 59, 7299. doi: 10.1021/jo00103a021
[52]	Molina, P.; Fresneda, P.; Sanz, M. J. Org. Chem. 1999, 64, 2540. doi: 10.1021/jo9819382
[53]	Liu, S.; Shao, J.; Guo, X.; Luo, J.; Zhao, M.; Zhang, G. L.; Yu, Y. P. Tetrahedron 2014, 70, 1418. doi: 10.1016/j.tet.2014.01.007
[54]	Guo, X.; Chen, W. T.; Chen, B. H.; Huang, W.; Qi, W. X.; Zhang, G. L.; Yu, Y. P. Org. Lett. 2015, 17, 1157. doi: 10.1021/acs.orglett.5b00289
[55]	Burnstock, G.; Verkhratsky, A. Acta. Physiol. 2009, 195, 415. doi: 10.1111/j.1748-1716.2009.01957.x
[56]	Murray, J. M.; Bussiere, D. E. Chemogenomics 2009, 575, 47.
[57]	Li, X.; Kang, H.; Liu, X.; Liu, Z.; Shu, K.; Chen, X.; Zhu, S. J. Huazhong Univ. Sci. Technol. Med. Sci. 2012, 32, 257.
[58]	Gillespie, R. J.; Bamford, S. J.; Botting, R. J. Med. Chem. 2009, 52, 33. doi: 10.1021/jm800961g pmid: 19072055
[59]	http://clinicaltrials.gov/ct2/show/NCT00442780
[60]	Kalinina, S. A.; Kalinin, D. V.; Dolzhenko, A. V. Tetrahedron Lett. 2013, 54, 5537. doi: 10.1016/j.tetlet.2013.07.158
[61]	Lim, F. P. L.; Luna, G; Dolzhenko, A. V. Tetrahedron Lett. 2015, 56, 7016. doi: 10.1016/j.tetlet.2015.11.006
[62]	Kalinin, D.; Kalinina, S.; Dolzhenko, A. Heterocycles 2013, 87, 147. doi: 10.3987/COM-12-12601
[63]	Lim, F. P. L.; Low, S. T.; Ho, E. L. K.; Halcovitch, N. R.; Tiekinkc, E. R. T.; Dolzhenko, A. V. RSC Adv. 2017, 7, 51062. doi: 10.1039/C7RA11305F
[64]	Li, T.; Senesi, A. J.; Lee, B. Chem. Rev. 2016, 116, 80. doi: 10.1021/acs.chemrev.5b00483
[65]	Mahfoudh, M.; Abderrahim, R.; Leclerc, E. Eur. J. Org. Chem. 2017, 2017, 2856. doi: 10.1002/ejoc.201700008
[66]	Zhang, L.; Fan, J.; Chong, J. H. Bioorg. Med. Chem. Lett. 2011, 21, 5633. doi: 10.1016/j.bmcl.2011.06.129 pmid: 21798738
[67]	Lim, S. M.; Xie, T.; Westover, K. D. Bioorg. Med. Chem. Lett. 2015, 25, 3382. doi: 10.1016/j.bmcl.2015.04.103
[68]	Venkatesan, G.; Paira, P.; Cheong, S. L. Bioorg. Med. Chem. Lett. 2014, 22, 1751. doi: 10.1016/j.bmc.2014.01.018
[69]	(a) Woller, K. R.; Curtin, M. L.; Frank, K. E.; Josephsohn, N. S.; Li, B. C.; Wishart, N. WO 156698, 2011.
	(b) Wainwright, P.; Maddaford, A.; Simms, M. Synlett 2011, 1900.
[70]	Tsai, S. E.; Yen, W. P.; Tseng, C. C.; Xie, J. J.; Liou, M. Y.; Li, Y. T.; Uramaru, N.; Wong, F. F. Tetrahedron 2018, 74, 2787. doi: 10.1016/j.tet.2018.04.048
[71]	Tseng, C. C.; Tsai S. E.; Li S. M. Wong, F. F. J. Org. Chem. 2019, 84, 16157. doi: 10.1021/acs.joc.9b02653
[72]	Seela, F.; Steker, H. Heterocycles 1985, 23, 2521. doi: 10.3987/R-1985-10-2521
[73]	Su, L.; Sun, K.; Pan, N.; Liu, L.; Sun, M. L.; Dong, J. Y.; Zhou, Y. B. Org. Lett. 2018, 20, 3399. doi: 10.1021/acs.orglett.8b01324
[74]	(a) Qiao, Q.; Dominique, R.; Goodnow, Jr. R. Tetrahedron Lett. 2008, 49, 3682. doi: 10.1016/j.tetlet.2008.03.140
	(b) Desroy, N.; Moreau, F.; Briet, S. Bioorg. Med. Chem. 2009, 17, 1276. doi: 10.1016/j.bmc.2008.12.021
[75]	Bey, E.; Marchais-Oberwinkler, S.; Werth, R. J. Med. Chem. 2008, 51, 6725. doi: 10.1021/jm8006917
[76]	Chalopin, T.; Dorta, D. A.; Sivignon, A. Org. Biomol Chem. 2016, 14, 3913. doi: 10.1039/c6ob00424e pmid: 27043998
[77]	Ishita, K.; Stefanopoulos, S.; Khalil, A. Bioorg. Med. Chem. 2018, 26, 2251.
[78]	Nettekoven, M.; Guba W.; Neidhart, W. ChemMedChem 2006, 1, 45. pmid: 16892333
[79]	Fu, R. G.; Wang, Y.; Xia, F. J. Org. Chem. 2019, 84, 12237. doi: 10.1021/acs.joc.9b02032
[80]	(a) Luo, L.; Meng, L.; Sun, Q. Tetrahedron Lett. 2014, 55, 259. doi: 10.1016/j.tetlet.2013.11.014
	(b) Gruner, M.; Boettcher, G.; Gewald, K. J. Heterocycl. Chem. 2008, 45, 1071. doi: 10.1002/jhet.5570450419
[81]	(a) Kumar, S. V.; Parameshwarappa, G.; Ila, H. J. Org. Chem. 2013, 78, 7362. doi: 10.1021/jo401208u pmid: 11950363
	(b) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2003, 5, 2911. pmid: 11950363
	(c) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2002, 4, 1363. pmid: 11950363
[82]	Guo, S.; Zhao, D.; Zhu, Y. Synth. Commun. 2017, 47, 1758. doi: 10.1080/00397911.2017.1350275
[83]	Avadhani, A.; Iniyavan, P.; Kumar, Y.; Ila, H. J. Org. Chem. 2021, 86, 8508. doi: 10.1021/acs.joc.1c00616 pmid: 34107686
[84]	(a) Romagnoli, R.; Baraldi, P. G.; Salvador, M. K. J. Med. Chem. 2012, 55, 5433. doi: 10.1021/jm300388h pmid: 22027100
	(b) Romagnoli, R.; Baraldi, P. G.; Cara, C. L. Eur. J. Med. Chem. 2011, 46, 6015. doi: 10.1016/j.ejmech.2011.10.013 pmid: 22027100
[85]	Kathiravan, M. K.; Salake, A. B.; Chothe, A. S. Bioorg. Med. Chem. 2012, 20, 5678. doi: 10.1016/j.bmc.2012.04.045
[86]	Mahfoudh, M.; Abderrahim, R.; Leclerc, E. Eur. J. Org. Chem. 2017, 2017, 2856. doi: 10.1002/ejoc.201700008
[87]	Chaurasia, S. R.; Dange, R.; Bhanage, B. M. Catal. Commun. 2020, 137, 105933. doi: 10.1016/j.catcom.2020.105933
[88]	Wolf, F. J.; Pfister 3rd. K.; Wilson, Jr, R. M.; Robinson, C. A. J. Am. Chem. Soc. 1954, 76, 3551. doi: 10.1021/ja01642a060
[89]	Belsky, A. J.; Li, T. J.; Brill, T. B. J. Supercrit. Fluids 1997, 10, 201. doi: 10.1016/S0896-8446(97)00022-3
[90]	Zhao, P.; Zhou, Y.; Yu, X. X. Huang, C.; Wu, Y. D.; Yin, G. D. Org. Lett. 2020, 22, 8528. doi: 10.1021/acs.orglett.0c03130
[91]	(a) Wu, C. P.; Lusvarghi, S.; Wang, J. C. Mol. Pharmaceutics 2019, 16, 3040. doi: 10.1021/acs.molpharmaceut.9b00274 pmid: 30807645
	(b) Grünewald, S.; Politz, O.; Bender, S. Int. J. Cancer 2019, 145, 1346. doi: 10.1002/ijc.32224 pmid: 30807645
	(c) Rouge, T. L. M.; Galluzzi, L.; Olaussen, K. A. Cancer Res. 2007, 67, 6253. doi: 10.1158/0008-5472.CAN-07-0538 pmid: 30807645
[92]	(a) Dixon, J. A.; Phillips, B.; Achebe, F.; Kluender, H. C. E.; Newcom, J.; Parcella, K.; Magnuson, S.; Hong, Z.; Zhang, Z.; Liu, Z.; Khire, U.; Wang, L.; Michels, M.; Chandler, B.; ,O’Connor S. US 8143393, 2006. pmid: 28851503
	(b) O'Connor, S.; Dumas, J.; Lee, W.; Dixon, J.; Cantin, D.; Gunn, D.; Burke, J.; Phillips, B.; Lowe, D.; Shelekhin, T.; Wang, G.; Ma, X.; Ying, S.; McClure, A.; Achebe, F.; Lobell, M.; Ehrgott, F.; Iwuagwu, C.; Parcella, K. US 8431695, 2006. pmid: 28851503
	(c) Song, Y.; Zhan, P.; Zhang, Q.; Liu, X. Curr. Pharm. Des. 2013, 19, 1528. pmid: 28851503
	(d) Cascioferro, S.; Parrino, B.; Spano, V.; Carbone, A.; Montalbano, A.; Barraja, P.; Diana, P.; Cirrincione, G. Eur. J. Med. Chem. 2017, 142, 328. doi: S0223-5234(17)30612-8 pmid: 28851503
[93]	Paymode, D. J.; Cardoso, F. S. P.; Agrawal, T.; Tomlin, J. W.; Cook, D. W.; Burns, J. M.; Stringham, R. W.; Sieber, J. D.; Snead, D. R. Org. Lett. 2020, 22, 7656. doi: 10.1021/acs.orglett.0c02848 pmid: 32931286
[94]	Knapp, R. R.; Tona, V.; Okada, T.; Sarpong, R.; Garg, N. K. Org. Lett. 2020, 22, 8430. doi: 10.1021/acs.orglett.0c03052
[95]	Wei, Z.; Zhang, Q.; Tang, M. Org. Lett. 2021, 23, 4436. doi: 10.1021/acs.orglett.1c01379
[96]	Liu, X.; Liu, H.; Bian, C.; Hu, Y. L. J. Org. Chem. 2022, 87, 5882. doi: 10.1021/acs.joc.2c00176

以氨基氰为原料合成含氮化合物的研究进展

Research Progress on the Synthesis of Nitrogen-Containing Compounds with Cyanamide as a Building Block

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 28

References 96

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Kangbo Feng, Jiong Chen, Shuangxi Gu, Haifeng Wang, Fen'er Chen. New Progress of Fully Continuous Flow Reaction Technologies in Pharmaceutical Synthesis (2019~2022) [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 378-397.
[2]	Chuanchuan Wang, Zhiwei Ma, Xuehui Hou, Longhua Yang, Yajing Chen. Research and Application of N-Ts Cyanamides in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 74-93.
[3]	Xinyi Ren, Guangzhu Wang, Xiaolei Ji, Kaiwu Dong. Synthesis of Two Types of Nitriles Both Bearing Quaternary Carbon Centers in One-Pot Manner [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 526-533.
[4]	Xiaojing Tian, Zhenzhen Fan, Si Jiang, Zhiwei Li, Jiangsheng Li, Yuefei Zhang, Cuihong Lu, Weidong Liu. Metal-Free Synthesis of Benzimidazo[1,2-c]quinazolines from N-Cyanobenzimidazoles via Double C—H Functionalizations [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3684-3692.
[5]	Yuan Zhu, Leyuan Chen, Wenbin Hou, Yiliang Li. Recent Progress in Nucleophilic Fluoride Mediated Fluorine-18 Labeling of Arenes and Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1774-1788.
[6]	Jiantao Zhang, Peng Zhou, Duoduo Xiao, Weibing Liu. Research Progress of 1,3,5-Triazinanes in the Synthesis of Nitrogen-Containing Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4154-4166.
[7]	Li Jihui, Li Zhengzhang, Zhang Yucang, Xu Wenrong, Xu Shuying. Progress on the Synthesis and Applications of Cyanamides [J]. Chin. J. Org. Chem., 2017, 37(8): 1903-1915.
[8]	Lu Wenyu, Yu Wenjing, Sun Dequn. Advances in Application of Marine Bioactive Peptides in Drug Development [J]. Chin. J. Org. Chem., 2017, 37(7): 1681-1700.
[9]	Huang Yanmin, Yao Qiucui, Liu Zhiping, Gan Chunfang, Zheng Jiahua, Sheng Haibing, Shi Haishing, Cui Jianguo. Synthesis and Antiproliferative Evaluation of Chenodeoxycholic Acid Containing-Nitrogen Derivatives [J]. Chin. J. Org. Chem., 2015, 35(10): 2168-2175.
[10]	SHU Long-Yi, SUN Hu, WANG Qian, TUN Shi. Progress in Binding Affinities of Metal Porphyrins to Heterocycles and DNA [J]. Chin. J. Org. Chem., 2009, 29(11): 1700-1707.
[11]	Li, Yunbo ; Tang, Fengxiang*; Meng, Chun; Guo, Yanghao. Progress in the Synthesis and Application of Nipecotic Acid and Its Derivatives [J]. Chin. J. Org. Chem., 2009, 29(07): 1068-1081.
[12]	WEI, Rong-Bao* ; LIU, Bo; LIU, Yang; GUO, Jin-Jing; ZHANG, Da-Wei. Progress in the Studies on Biological Activities of O, N or S-Containing Spiro Compounds [J]. Chin. J. Org. Chem., 2008, 28(9): 1501-1514.
[13]	LI,Lu; ZHANG, Gui-Sheng*. Progress in Syntheses of Uncommon Sugars [J]. Chin. J. Org. Chem., 2008, 28(07): 1129-1137.
[14]	He Hongwu. Phosphorus chemistry,A field full of vitality and scientific opportunities [J]. Chin. J. Org. Chem., 2003, 23(2): 155-161.
[15]	Liu Liu;Zhang Haitao;Wang Yunpu. Syntheses of water-soluble polymer-supported ferrocenyl schiff bases [J]. Chin. J. Org. Chem., 2002, 22(4): 286-288.