Citation: Tang Zilong, Wang Ming, Yao Yuan, Tan Jingzhao, Dai Ningning, Li Xinxing, Peng Lifen, Jiao Yinchun. Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes[J]. Chinese Journal of Organic Chemistry, ;2019, 39(3): 800-810. doi: 10.6023/cjoc201808003 shu

Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes

Tang Zilong ^a,b,, ,
Wang Ming ^a,b ,
Yao Yuan ^a,b ,
Tan Jingzhao ^a,b ,
Dai Ningning ^a,b ,
Li Xinxing ^a,b ,
Peng Lifen ^a ,
Jiao Yinchun ^b

a.
Key Laboratory of Theoretical Organic Chemistry and Functional Molecular, Ministry of Education, Hunan University of Science and Technology, Xiangtan 411201
b.
Hunan Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201

Corresponding author: Tang Zilong, zltang67@aliyun.com
Received Date: 6 August 2018
Revised Date: 10 September 2018
Available Online: 26 March 2018
Fund Project: the National Natural Science Foundation of China 21372070the Scientific Research Fund of Hunan Provincial Education Department 17A066the National Natural Science Foundation of China 21877034Project supported by the National Natural Science Foundation of China (Nos. 21877034, 21372070) and the Scientific Research Fund of Hunan Provincial Education Department (No. 17A066)

Figures(4)

Lewis acid La(OTf) ₃-catalyzed chemoselective cyclization of hydroxyl substituted ethylenediamine derivatives with aldehydes has been described for the first time, which provides efficient access to diversely functionalized 1, 3-imidazoli-dines and 3, 1-benzoxazines in generally good yields only by adjusting the position of the methylene group within hydroxyl substituted ethylenediamines. The reaction is suitable to aromatic aldehydes and aliphatic ones. Plausible mechanisms are also proposed to explain the observed reaction modes, wherein the nucleophilicity of nitrogen and oxygen atoms plays an important role in controlling the chemoselectivity.
- hydroxyl substituted ethylenediamine,
- 1, 3-imidazolidine,
- 3, 1-benzoxazine,
- chemoselectivity,
- synthesis
1. [1]
  Neuvonen, K.; Pihlaja, K. J. Chem. Soc., Perkin Trans 2 1988, 461.
2. [2]
  Tang, Z.; Chen, W.; Zhu, Z.; Liu, H. J. Heterocycl. Chem. 2011, 48, 255. doi: 10.1002/jhet.533
3. [3]
  Mangion, K.; Chen, C.; Li, H.; Maligres, P.; Chen, Y.; Christensen, M.; Cohen, R.; Jeon, I.; Klapars, A.; Krska, S.; Nguyen, H.; Reamer, R. A.; Sherry, B. D.; Zavialov, I. Org. Lett. 2014, 16, 2310. doi: 10.1021/ol500971c
4. [4]
  Tang, Z.; Chen, W.; Zhu, Z.; Liu, H. Synth. Commun. 2012, 42, 1372. doi: 10.1080/00397911.2010.540691
5. [5]
  Mathew, B. P.; Nath, M. J. Heterocycl. Chem. 2009, 46, 1003. doi: 10.1002/jhet.v46:5
6. [6]
  Colin, J. L.; Loubinoux, B. Tetrahedron Lett. 1982, 23, 4245. doi: 10.1016/S0040-4039(00)88715-8
7. [7]
  Richers, M. T.; Breugst, M.; Platonova, A. Y.; Ullrich, A.; Dieckmann, A.; Houk, K. N.; Seidel, D. J. Am. Chem. Soc. 2014, 136, 6123. doi: 10.1021/ja501988b
8. [8]
  Xu, F.; Qian, X.-Y.; Li, Y.-J.; Xu, H.-C. Org. Lett. 2017, 19, 6332. doi: 10.1021/acs.orglett.7b03152
9. [9]
  Chen, X.; Hao, W.; Liu, Y. Org. Biomol. Chem. 2017, 15, 3423. doi: 10.1039/C7OB00625J
10. [10]
  Garg, V.; Kumar, A.; Chaudhary, A.; Agrawal, S.; Tomar, P.; Sreenivasan, K. K. Med. Chem. Res. 2013; 22, 5256. doi: 10.1007/s00044-013-0534-3
11. [11]
  Chen, Y.; Cass, S. L.; Kutty, S. K.; Yee, E. M. H.; Chan, D. S. H.; Gardner, C. R.; Vittorio, O.; Pasquier, E.; Black, D. S.; Kumar, N.; Bioorg. Med. Chem. Lett. 2015, 25, 5377. doi: 10.1016/j.bmcl.2015.09.027
12. [12]
  Morrison, R.; Al-Rawi, J. M. A.; Jennings, I.; Thompson, P. E. Eur. J. Med. Chem. 2016, 110, 326. doi: 10.1016/j.ejmech.2016.01.042
13. [13]
  Ihmaid, S. K.; Ai-Rawi, J. M. A.; Bradley, C. J.; Angove, M. J.; Robertson, M. N. Eur. J. Med. Chem. 2012, 57, 85. doi: 10.1016/j.ejmech.2012.08.035
14. [14]
  Nemecek. P.; Mocak, J.; Lehotay, J.; Waisser, K. Chem. Papers 2013, 67, 305.
15. [15]
  Pastemak, A.; Goble, S. D.; Struters, M.; Vicario, P. P.; Ayala, J. M.; Salvo, J. D.; Kilbum, R.; Wisniewski, T.; Demartino, J. A.; Mills, S. G.; Yang, L. ACS Med. Chem. Lett. 2010, 1, 14. doi: 10.1021/ml900009d
16. [16]
  Tong, L.; Yu, W.; Chen, L.; Selyutin, O.; Dwyer, M. P.; Nair, A. G.; Mazzola, R.; Kim, J.; Sha, D.; Yin, J.; Ruck, R. T.; Davies, I. W.; Hu, B.; Zhong B.; Hao, J.; Ji, T.; Zan, S.; Liu, R.; Agrawal, S.; Xia, E.; Curry, S.; McMonagle, P.; Bystol, K.; Lahser, F.; Carr, D.; Rokosz, L.; Ingravallo, P.; Chen, S.; Feng, K.; Cartwright, M.; Asante-Appiah, E.; Kozlowski, J. A. J. Med. Chem. 2017, 60, 290. doi: 10.1021/acs.jmedchem.6b01310
17. [17]
  Ihmaid, S.; Ahmed, H. E. A.; Ali, A. A.; Sherif, Y. E.; Tarazi, H. M.; Riyadh, S. M.; Zayed, M. F.; Abulkhair, H. S.; Rateb, H. S. Bioorg. Chem. 2017, 72, 234. doi: 10.1016/j.bioorg.2017.04.014
18. [18]
  Sharma, V.; Amarnath, N.; Shukla, S.; Ayana, R.; Kumar, N.; Yadav, N.; Kannan, D.; Sehrawat, S.; Pati, S.; Lochab, B.; Singh, S.; Bioorg. Med. Chem. Lett. 2018, 28, 1629. doi: 10.1016/j.bmcl.2018.03.047
19. [19]
  Zhang, P.; Terefenko, E. A.; Fensome, A.; Zhang, Z.; Zhu, Y.; Cohen, J.; Winneker, R.; Wrobel, J.; Yardley, J. Bioorg. Med. Chem. Lett. 2002, 12, 787. doi: 10.1016/S0960-894X(02)00025-2
20. [20]
  Nguyen, T. T.; Amey, R. L.; Martin, J. C. J. Org. Chem. 1982, 47, 1024. doi: 10.1021/jo00345a026
21. [21]
  Kobzina, J. W.; Creek, W. US 4030906, 1977.
22. [22]
  Sugiyama, H.; Hosoda, K.; Kumagai, Y.; Takeuchi, M.; Okada, M. U. US 4596801, 1986.
23. [23]
  Charmantray, F.; Demeunynck, M.; Carrez, D.; Croisy, A.; Lansiaux, A.; Bailly, C.; Colson, P. J. Med. Chem. 2003, 46, 967. doi: 10.1021/jm020389w
24. [24]
  Badolato, M.; Carullo, G.; Armentano, B.; Panza, S.; Malivindi, R. Bioorg. Med. Chem. Lett. 2017, 27, 3092. doi: 10.1016/j.bmcl.2017.05.046
25. [25]
  Dias, N.; Goossens, J.; Baldeyrou, B.; Lansiaux, A.; Colson, P.; Di Salvo, A.; Bernal, J.; Turnbull, A.; Mincher, D. J.; Bailly, C. Bioconjugate Chem. 2005, 16, 949. doi: 10.1021/bc050065x
26. [26]
  Marasini, B. P.; Rahim, F.; Perveen, S.; Karim, A.; Khan, K. M.; Rahman, A.; Choudhary, M. L. Bioorg. Chem. 2017, 70, 210. doi: 10.1016/j.bioorg.2017.01.001
27. [27]
  Braga, A. L.; Vargas, F.; Silveira, C. C.; de Andrade, L. H. Tetrahedron Lett. 2002, 43, 2335. doi: 10.1016/S0040-4039(02)00300-3
28. [28]
  Lee, E.; Kim, S.; Jung, B.; Ahn, W.; Kim, G. Tetrahedron Lett. 2003, 44, 1971. doi: 10.1016/S0040-4039(03)00069-8
29. [29]
  Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338. doi: 10.1021/ja100265j
30. [30]
  Wang, Y.; Zhang, H.; Li, C.; Fan, T.; Shi, F. Chem. Commun. 2016, 52, 1804. doi: 10.1039/C5CC07924A
31. [31]
  Matosiuk, D.; Fidecka, S.; Antkiewicz-Michaluk, L.; Dybala, I.; Koziol, A. E. Eur. J. Med. Chem. 2001, 36, 783. doi: 10.1016/S0223-5234(01)01267-3
32. [32]
  Byrtus, H.; Obniska, J.; Czopek, A.; Kaminski, K.; Pawlowski, M. Bioorg. Med. Chem. 2011, 19, 6149. doi: 10.1016/j.bmc.2011.08.017
33. [33]
  Kim, M.; Kim, H.; Kim, H.; Chin, J. J. Org. Chem. 2017, 82, 12050. doi: 10.1021/acs.joc.7b01751
34. [34]
  Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Rev. 2015, 115, 5301. doi: 10.1021/cr5006974
35. [35]
  Chen, D. Z.; Xiao, W. J.; Chen, J. R. Org. Chem. Front. 2017, 4, 1289. doi: 10.1039/C7QO00163K
36. [36]
  Tang, Z.; Tan, J.; Cai, L.; Li, X.; Liu, W. Chin. J. Appl. Chem. 2017, 34, 345.
37. [37]
  CCDC 1823294 for compound 5ba, see the Supporting Information for detail.
38. [38]
  Tang, Z.; Wang, L.; Tan, J.; Yao, Y.; Peng, L. Chin. J. Appl. Chem. 2018 35, 1190.
1. [1]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
2. [2]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
3. [3]
  Kun Wang , Tianxue Gong , Yaohuang Huang , Boyang Han , Hanxiao Yang , Pavlo O. Dral , Weiwei Fang . Bornylimidazo[1,5–a]pyridin-3-ylidene allylic Pd catalyst with optimal electronic and steric properties for synthesis of 3,3′-disubstituted oxindoles. Chinese Chemical Letters, 2025, 36(7): 110539-. doi: 10.1016/j.cclet.2024.110539
4. [4]
  Rong-Nan Yi , Wei-Min He . Photocatalytic Minisci-type multicomponent reaction for the synthesis of 1-(halo)alkyl-3-heteroaryl bicyclo[1.1.1]pentanes. Chinese Chemical Letters, 2024, 35(10): 110115-. doi: 10.1016/j.cclet.2024.110115
5. [5]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
6. [6]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
7. [7]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
8. [8]
  Bin SUN , Heyan JIANG . Glucose-modified bis-Schiff bases: Synthesis and bio-activities in Alzheimer′s disease therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1338-1350. doi: 10.11862/CJIC.20240428
9. [9]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
10. [10]
  Lixing ZHANG , Yaowen WANG , Xu HAN , Junhong ZHOU , Jinghui WANG , Liping LI , Guangshe LI . Research progress in the synthesis of fluorine-containing perovskites and their derivatives. Chinese Journal of Inorganic Chemistry, 2025, 41(9): 1689-1701. doi: 10.11862/CJIC.20250007
11. [11]
  Wujun Jian , Mong-Feng Chiou , Yajun Li , Hongli Bao , Song Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980
12. [12]
  Weizhong LING , Jingyi LIN , Jianglin ZHU , Yuyi LIANG , Shanshan DAI , Yu LI . Syntheses, structures, and catalytic performances of complexes with 4,4′-dihydroxy-[1,1′-biphenyl]-3,3′-dicarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 152-160. doi: 10.11862/CJIC.20250204
13. [13]
  Zhiwei Chen , Heyun Sheng , Xue Li , Menghan Chen , Xin Li , Qiuling Song . Efficient capture of difluorocarbene by pyridinium 1,4-zwitterionic thiolates: A concise synthesis of difluoromethylene-containing 1,4-thiazine derivatives. Chinese Chemical Letters, 2024, 35(4): 108937-. doi: 10.1016/j.cclet.2023.108937
14. [14]
  Qi Li , Zi-Lu Wang , Yun-He Xu . Copper-catalyzed 1,4-silylcyanation of 1,3-enynes: A silyl radical-initiated approach for synthesis of difunctionalized allenes. Chinese Chemical Letters, 2025, 36(3): 109991-. doi: 10.1016/j.cclet.2024.109991
15. [15]
  Chao LIU , Jiang WU , Zhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153
16. [16]
  Yueying Yang , Huiru Xie , Xinbo Yu , Yang Liu , Hui Wang , Hua Li , Lixia Chen . Design, synthesis and evaluation of the first DYRK1A degrader for promoting the proliferation of pancreatic β-cells. Chinese Chemical Letters, 2024, 35(11): 109570-. doi: 10.1016/j.cclet.2024.109570
17. [17]
  Yongli Zhao , Dingsheng Cao , Jie-Ping Wan , Yunyun Liu . Synthesis of 3-phosphinyl chromones via in situ iodination mediated C-H phosphination and the tunable synthesis of 2-phosphoryl chromanones. Chinese Chemical Letters, 2026, 37(1): 111740-. doi: 10.1016/j.cclet.2025.111740
18. [18]
  Yanfen PENG , Xinyue WANG , Tianbao LIU , Xiaoshuo WU , Yujing WEI . Syntheses and luminescence of four Cd(Ⅱ)/Zn(Ⅱ) complexes constructed by 1,3‐bis(4H‐1,2,4‐triazole)benzene. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1416-1426. doi: 10.11862/CJIC.20250018
19. [19]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
20. [20]
  Bairu Meng , Zongji Zhuo , Han Yu , Sining Tao , Zixuan Chen , Erik De Clercq , Christophe Pannecouque , Dongwei Kang , Peng Zhan , Xinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827

Get Citation

PDF

XML

Metrics

PDF Downloads(8)
Abstract views(1691)
HTML views(119)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142