研究论文

室温条件下“一锅多组分”脯氨酸催化合成N,O-缩醛化合物

  • 兰金 ,
  • 谢宗波 ,
  • 杨江楠 ,
  • 孟佳 ,
  • 刘一帅 ,
  • 乐长高
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  • 东华理工大学应用化学系 南昌 330013

收稿日期: 2019-11-06

  修回日期: 2019-12-19

  网络出版日期: 2020-01-21

基金资助

国家自然科学基金(Nos.21462001,11765002)、江西省科技计划(No.20161BCB24006)、江西省教育厅科技(Nos.KJLD14050,GJJ150584)资助项目.

One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature

  • Lan Jin ,
  • Xie Zongbo ,
  • Yang Jiangnan ,
  • Meng Jia ,
  • Liu Yishuai ,
  • Le Zhanggao
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  • Department of Applied Chemistry, East China University of Technology, Nanchang 330013

Received date: 2019-11-06

  Revised date: 2019-12-19

  Online published: 2020-01-21

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21462001, 11765002), the Science and Technology Projects of Jiangxi Province (No. 20161BCB24006), and the Science and Technology Foundation of Jiangxi Provincial Department of Education (Nos. KJLD14050, GJJ150584).

摘要

以芳香醛、脲和醇为原料,过量的醇为溶剂,D-脯氨酸为催化剂,开发了一种简单的多组分一锅法合成NO-缩醛化合物的方法.在室温下反应30 h后,以良好的收率合成了一系列NO-缩醛化合物.

本文引用格式

兰金 , 谢宗波 , 杨江楠 , 孟佳 , 刘一帅 , 乐长高 . 室温条件下“一锅多组分”脯氨酸催化合成N,O-缩醛化合物[J]. 有机化学, 2020 , 40(5) : 1331 -1336 . DOI: 10.6023/cjoc201911010

Abstract

In this paper, a convenient method for multi-component one-pot synthesis of N,O-acetal compounds was developed, using aromatic aldehyde, urea and alcohol as materials, alcohol also as solvent and D-proline as catalyst. A series of N,O-acetal compounds were synthesized in good yields after reacting for 30 h at room temperature.

参考文献

[1] Li, G.; Fronczek, F. R.; Antilla, J. C. J. Am. Chem. Soc. 2008, 130, 12216.
[2] Tanaka, J. I.; Higa, T. Tetrahedron Lett. 1996, 37, 5535.
[3] Jiang, X.; Williams, N.; De Brabander, J. K. Org. Lett. 2007, 9, 227.
[4] Chen, G.; Patanapongpibul, M.; Jiang, Z.; Zhang, Q.; Zheng, S.; Wang, G.; White, J. D.; Chen, Q. H. Org. Biomol. Chem. 2019, 17, 3830.
[5] Mosey, R. A.; Floreancig, P. E. Nat. Prod. Rep. 2012, 29, 980.
[6] Li, M.; Luo, B.; Liu, Q.; Hu, Y.; Ganesan, A.; Huang, P.; Wen, S. Org. Lett. 2013, 16, 10.
[7] Huang, Y. Y.; Cai, C.; Yang, X. ACS Catal. 2016, 6, 5747.
[8] Downey, C. W.; Lee, A. Y. K.; Goodin, J. R.; Botelho, C. J.; Stith, W. M. Tetrahedron Lett. 2017, 58, 3496.
[9] Zhang, Q.; Xu, D.; Yang, J.; He, L.; Zhang, M. Tetrahedron Lett. 2019, 60, 150992.
[10] Fletcher, J. T.; Christensen, J. A.; Villa, E. M. Tetrahedron Lett. 2017, 58, 4450.
[11] Traboni, S.; Bedini, E.; Giordano, M.; Iadonisi, A. Tetrahedron Lett. 2019, 60, 1777.
[12] Lillo, V. J.; Mansilla, J.; Saá, J. M. Org. Biomol. Chem. 2018, 16, 4527.
[13] Wan S. Y.; Green, M. E.; Park, J. H.; Floreancig, P. E. Org. Lett. 2007, 9, 5385.
[14] Danson, K. J. Y.; Richard, J. A. Tetrahedron Lett. 2014, 55, 2183.
[15] Narina, S. V.; Sudalai, A. Tetrahedron Lett. 2006, 47, 6799.
[16] Basumatary, G.; Mohanta, R.; Bez, G. Catal. Lett. 2019, 149, 2776.
[17] Wu, H.; Liu, H.; Li, J.; Li, X.; Xiao, H. P.; Jiang, J. Synlett 2019, 30, 1241.
[18] Lucas, F. D. C.; Simone, C. S.; Matheus, V. M.; Paloma, S. P.; Alberto, W. J.; Diogo, M. V.; José Augusto, F. P. V. J. Braz. Chem. Soc. 2018, 30, 893.
[19] Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600.
[20] Bhattacharjee, D.; Sutradhar, D.; Chandra, A. K.; Myrboh, B. Tetrahedron 2017, 73, 3497.
[21] König, S.; Marco, H.; Gäde, G. Amino Acids 2017, 50, 359.
[22] Allen, W. D.; Czinki, E.; Csaszar, A. G. Chem.-Eur. J. 2004, 10, 4512.
[23] Usui, I.; Schmidt, S.; Breit, B. Org. Lett. 2009, 11, 1453.
[24] Morales, S.; Guijarro, F. G.; García Ruano, J. L.; Cid, M. B. J. Am. Chem. Soc. 2014, 136, 1082.
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