SIOC English
有机化学
高级检索

有机化学 >

2013 , Vol. 33 >Issue 10: 2232 - 2236

DOI: https://doi.org/10.6023/cjoc201304040

研究简报

磺酸功能化的聚乙二醇6000催化下合成二氢吡咯酮类化合物

  • 田拴宝 ,
  • 郝永兵
展开
  • 新乡医学院基础医学院 新乡 453003

收稿日期: 2013-04-24

  修回日期: 2013-06-07

  网络出版日期: 2013-06-21

收起

Sulfuric Acid-Modified Polyethylene Glycol 6000 Catalyzed Synthesis of Dihydropyrrolone

  • Tian Shuanbao ,
  • Hao Yongbing
Expand
  • School of Basic Medical Sciences, Xinxiang Medical University, Xinxiang 453003

Received date: 2013-04-24

  Revised date: 2013-06-07

  Online published: 2013-06-21

Fold

摘要

以磺酸功能化的聚乙二醇6000为催化剂, 在室温和甲醇作为溶剂的条件下, 通过两种相同或不同的胺, 丁-2-炔二酯和甲醛四组分缩合, 高收率地实现了一系列二氢吡咯酮类化合物的合成. 产物结构经1H NMR, 13C NMR, IR, 元素分析等进行了表征.

关键词： 二氢吡咯酮类化合物; 磺酸功能化的聚乙二醇6000; 丁-2-炔二酯; 多组分反应; 合成

本文引用格式

田拴宝 , 郝永兵 . 磺酸功能化的聚乙二醇6000催化下合成二氢吡咯酮类化合物[J]. 有机化学, 2013 , 33(10) : 2232 -2236 . DOI: 10.6023/cjoc201304040

Abstract

A series of dihydropyrrolones were synthesized in high yields by reaction of two same/different primary amines, but-2-ynedioates and formaldehyde in the presence of sulfuric acid-modified polyethylene glycol 6000 in MeOH at room temperature. All products were characterized by 1H NMR, 13C NMR, IR and elemental analysis.

Key words： dihydropyrrolones; sulfuric acid-modified polyethylene glycol 6000; but-2-ynedioates; multi-component reaction; synthesis

参考文献

[1] Li, B.; Lyle, M. P. A.; Chen, G.; Li, J.; Hu, K.; Tang, L.; Alaoui-Jamali, M. A.; Webster, J. Bioorg. Med. Chem. 2007, 15, 4601.
[2] Demir, A. S.; Aydigan, F.; Akhmedov, I. M. Tetrahedron: Asymmetry 2002, 13, 601.
[3] Zhang, L.; Tan, Y.; Wang, N.-X.; Wu, Q.-Y.; Xi, Z.; Yang, G.-F. Bioorg. Med. Chem. 2010, 18, 7948.
[4] Mizushina, Y.; Kobayashi, S.; Kuramochi, K.; Nagata, S.; Sugawara, F.; Sakaguchi, K. Biochem. Biophys. Res. Commun. 2000, 273, 784.
[5] Li, W. R.; Lin, S. T.; Hsu, N. M.; Chern, M. S. J. Org. Chem. 2002, 67, 4702.
[6] Zhao, Y.; Wang, Q.; Meng, Q.; Ding, D.; Yang, H.; Gao, G.; Li, D.; Zhu, W.; Zhou, H. Bioorg. Med. Chem. 2012, 20, 1240.
[7] Kawasuji, T.; Fuji, M.; Yoshinaga, T.; Sato, A.; Fujiwara, T.; Kiyama, R. Bioorg. Med. Chem. 2007, 15, 5487.
[8] Bellur, E.; Langer, P. Tetrahedron Lett. 2006, 47, 2151
[9] Bach, T.; Brummerhop, H. Angew. Chem., Int. Ed. 1998, 37, 3400.
[10] (a) Kawase, M.; Hirabayashi, M.; Saito, S.; Yamamoto, K. Tetrahedron Lett. 1999, 40, 2541.
(b) Metten, B.; Kostermans, M.; Van Baelen, G.; Smet, M.; Dehaen, W. Tetrahedron 2006, 62, 6018.
(c) Albrecht, D.; Basler, B.; Bach, T. J. Org. Chem. 2008, 73, 2345.
[11] Lv, L.; Zheng, S.; Cai, X.; Chen, Z.; Zhu, Q.; Liu, S. ACS Comb. Sci. 2013, 15, 183.
[12] Sajadikhah, S. S.; Hazeri, N.; Maghsoodlou, M. T.; Habibi-Khorassani, S. M.; Khandan-Barani, K. J. Chem. Res. 2013, 37, 40.
[13] Khan, A. T.; Md, A. G.; Khan, M. Tetrahedron Lett. 2012, 53, 2622.
[14] (a) Zhang, Z.; Du, B.; Zhang, L.-J.; Da, Y.-X.; Quan, Z.-J.; Yang, L.-J.; Wang, X.-C. RSC Adv. 2013, 3, 9201.
(b) Paul, S.; Das, A. R. Tetrahedron Lett. 2013, 54, 1149.
(c) Hasaninejed, A.; Kazerooni, M. R.; Zare, A. Catal. Today 2012, 196, 148.
(d) Shekouhy, M. Catal. Sci. Technol. 2012, 2, 1010.
(e) Kiasat, A.; Mehrjardi, M. F. Catal. Commun. 2008, 9, 1497.
(f) Wang, X.; Quan, Z.; Wang, F.; Wang, M.; Zhang, Z.; Li, Z. Synth. Commun. 2006, 36, 451.
(g) Hasaninejad, A.; Zare, A.; Shekouhy, M. Tetrahedron 2011, 67, 390.
Options
文章导航

/

〈 〉