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

doi:10.6023/cjoc201808003

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (3): 800-810.DOI: 10.6023/cjoc201808003 Previous Articles Next Articles

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羟基取代乙二胺衍生物与醛反应化学选择性合成取代苯并噁嗪和咪唑啉

唐子龙^a,b, 汪明^a,b, 姚园^a,b, 谭经照^a,b, 代宁宁^a,b, 李新兴^a,b, 彭丽芬^a, 焦银春^b

a 湖南科技大学理论有机化学与功能分子教育部重点实验室湘潭 411201;
b 湖南科技大学化学化工学院精细聚合物可控制备及功能应用湖南省重点实验室湘潭 411201

收稿日期:2018-08-06 修回日期:2018-09-10 发布日期:2018-10-26
通讯作者: 唐子龙 E-mail:zltang67@aliyun.com
基金资助:
国家自然科学基金（Nos.21877034，21372070）和湖南省教育厅科学研究基金（No.17A066）.

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

Received:2018-08-06 Revised:2018-09-10 Published:2018-10-26
Contact: 10.6023/cjoc201808003 E-mail:zltang67@aliyun.com
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21877034, 21372070) and the Scientific Research Fund of Hunan Provincial Education Department (No. 17A066).

1. Chemoselective Synthesis of Substituted Benzoxazines and Imidazolidines by Reactions of Hydroxyl Substituted Ethylenediamine Derivatives with Aldehydes.PDF(4598KB)

Abstract

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.

Key words: hydroxyl substituted ethylenediamine, 1,3-imidazolidine, 3,1-benzoxazine, chemoselectivity, synthesis

Cite this article

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]. Chin. J. Org. Chem., 2019, 39(3): 800-810.

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[1] Neuvonen, K.; Pihlaja, K. J. Chem. Soc., Perkin Trans 2 1988, 461.
[2] Tang, Z.; Chen, W.; Zhu, Z.; Liu, H. J. Heterocycl. Chem. 2011, 48, 255.
[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.
[4] Tang, Z.; Chen, W.; Zhu, Z.; Liu, H. Synth. Commun. 2012, 42, 1372.
[5] Mathew, B. P.; Nath, M. J. Heterocycl. Chem. 2009, 46, 1003.
[6] Colin, J. L.; Loubinoux, B. Tetrahedron Lett. 1982, 23, 4245.
[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.
[8] Xu, F.; Qian, X.-Y.; Li, Y.-J.; Xu, H.-C. Org. Lett. 2017, 19, 6332.
[9] Chen, X.; Hao, W.; Liu, Y. Org. Biomol. Chem. 2017, 15, 3423.
[10] Garg, V.; Kumar, A.; Chaudhary, A.; Agrawal, S.; Tomar, P.; Sreenivasan, K. K. Med. Chem. Res. 2013; 22, 5256.
[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.
[12] Morrison, R.; Al-Rawi, J. M. A.; Jennings, I.; Thompson, P. E. Eur. J. Med. Chem. 2016, 110, 326.
[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.
[14] Nemecek. P.; Mocak, J.; Lehotay, J.; Waisser, K. Chem. Papers 2013, 67, 305.
[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.
[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.
[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.
[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.
[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.
[20] Nguyen, T. T.; Amey, R. L.; Martin, J. C. J. Org. Chem. 1982, 47, 1024.
[21] Kobzina, J. W.; Creek, W. US 4030906, 1977.
[22] Sugiyama, H.; Hosoda, K.; Kumagai, Y.; Takeuchi, M.; Okada, M. U. US 4596801, 1986.
[23] Charmantray, F.; Demeunynck, M.; Carrez, D.; Croisy, A.; Lansiaux, A.; Bailly, C.; Colson, P. J. Med. Chem. 2003, 46, 967.
[24] Badolato, M.; Carullo, G.; Armentano, B.; Panza, S.; Malivindi, R. Bioorg. Med. Chem. Lett. 2017, 27, 3092.
[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.
[26] Marasini, B. P.; Rahim, F.; Perveen, S.; Karim, A.; Khan, K. M.; Rahman, A.; Choudhary, M. L. Bioorg. Chem. 2017, 70, 210.
[27] Braga, A. L.; Vargas, F.; Silveira, C. C.; de Andrade, L. H. Tetrahedron Lett. 2002, 43, 2335.
[28] Lee, E.; Kim, S.; Jung, B.; Ahn, W.; Kim, G. Tetrahedron Lett. 2003, 44, 1971.
[29] Arai, T.; Mishiro, A.; Yokoyama, N.; Suzuki, K.; Sato, H. J. Am. Chem. Soc. 2010, 132, 5338.
[30] Wang, Y.; Zhang, H.; Li, C.; Fan, T.; Shi, F. Chem. Commun. 2016, 52, 1804.
[31] Matosiuk, D.; Fidecka, S.; Antkiewicz-Michaluk, L.; Dybala, I.; Koziol, A. E. Eur. J. Med. Chem. 2001, 36, 783.
[32] Byrtus, H.; Obniska, J.; Czopek, A.; Kaminski, K.; Pawlowski, M. Bioorg. Med. Chem. 2011, 19, 6149.
[33] Kim, M.; Kim, H.; Kim, H.; Chin, J. J. Org. Chem. 2017, 82, 12050.
[34] Chen, J. R.; Hu, X. Q.; Lu, L. Q.; Xiao, W. J. Chem. Rev. 2015, 115, 5301.
[35] Chen, D. Z.; Xiao, W. J.; Chen, J. R. Org. Chem. Front. 2017, 4, 1289.
[36] Tang, Z.; Tan, J.; Cai, L.; Li, X.; Liu, W. Chin. J. Appl. Chem. 2017, 34, 345.
[37] CCDC 1823294 for compound 5ba, see the Supporting Information for detail.
[38] Tang, Z.; Wang, L.; Tan, J.; Yao, Y.; Peng, L. Chin. J. Appl. Chem. 2018 35, 1190.

羟基取代乙二胺衍生物与醛反应化学选择性合成取代苯并噁嗪和咪唑啉

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

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